What Might've Been
by Ultrawoman
Summary: Jess is sent to live with his Uncle Luke around the same time that Lorelai and Rory move into their house in Stars Hollow. Getting to know each other from age eleven leads to an evolved relationship for Rory and Jess that was never romantic, but as the best friends reach age sixteen, what might change? (AU, will be Rory/Jess and Luke/Lorelai eventually)
1. Prologue - Wacky Coincidence

**A/N: So I had this idea, and I have noticed there are some other stories out there on a similar theme BUT I think mine is going to be different enough to be good. Please bear in mind that this is just the prologue to set up the way things are different in this AU. The actual fic isn't going to be about kids, it's going to be about the teenaged Rory & Jess we know and love as of next chapter when the story truly starts.**

_**Disclaimer: All recognisable characters belong to Amy Sherman-Palladino and other folks that aren't me.**_

Prologue - Wacky Coincidence

"Rory, will you slow down a little?!" Lorelai called to her daughter. "We're not going to be late, I promise."

Immediately she said it, she checked her watch, only to realise that maybe she just told her impressionable eleven year old a big fat fib. It wasn't deliberate. Lorelai really had believed they had time to spare, but apparently not. Maybe it would've been better if she got out of bed the first time the alarm clock rang, maybe even the fourth time, maybe even when Rory came and shoved her for the ninth time and asked her to move herself already. It didn't matter. They were in sight of the school now and everything would be fine. Lorelai had no worries about Rory getting on just fine at Stars Hollow Middle School. The kid was smart, clean, polite, there should be no problems. Lorelai couldn't explain then why her heart was beating a mile a minute as she hurried after her baby girl towards the school.

"Geez, I swear one day I'm gonna figure out how you ever got so fast!" she muttered as she followed Rory as far as the steps, grabbing at her wrist before she could completely get away. "Not so fast, missy," she told her.

"Sorry, Mom," said Rory with a bashful smile, "I just can't wait to see the place. The classrooms, the library, meeting my teachers and all the new kids."

"Hey, I'm glad you're excited. Never been so happy about anything," Lorelai assured her. "But, y'know, Mommy's feeling the nerves here. Everything is just changing so fast and you're growing up and... and I'm having a little emotional moment," she realised too late as tears came to her eyes.

"Oh, Mom!" Rory gasped at the sight of her mother's upset, throwing herself at her to give her a big hug. "It's gonna be fine. I love that we moved here. I mean, yeah, I know I cried a lot when you said we had to leave our old place, but Stars Hollow seems nice and I just know school is gonna be fine."

"Stars Hollow seems nice?" asked Lorelai, pulling out of their hug but still keeping hold of her daughter yet. "Hon, we only moved into the place three days ago, and you barely left the house yet," she smiled fondly. "You can't know if a place is nice that fast."

"I have a good feeling," Rory grinned widely. "You know I'm never wrong about this stuff."

"That's right. You got your 'good feeling' skills from your Momma," Lorelai smiled right back, pressing Rory's nose like a button and making her laugh. "Okay," she said then, clearing her throat and straightening up. "Back pack, books, 2B pencils," she reeled off.

"Yes, yes, and yes," Rory dutifully checked off the list. "Also, lunch money, gym clothes, and emergency lip gloss."

"That's my girl," Lorelai sighed, finding it hard to believe this was in fact her baby girl, growing up so fast.

It seemed like only yesterday when she born, saying her first word, taking her first steps. For eleven years, Rory had been raised in a converted potting shed behind the Independence Inn, with help from the owner, Mia, and many of the staff. Lorelai had worked her way up from maid to waitress to assistant manager. Enough hard work and she planned to be running the place before long. Now she and Rory could at least afford to live in their own home, albeit it needed some work done yet. The point was, they were doing okay, the eleven year old who had read more books than most adults, and her twenty seven year old mother who had grown up in double-quick time, out of pure necessity.

"Okay, so..." Lorelai began her goodbye to Rory, only to be interrupted by a yelling that started up somewhere behind her.

"I'm not goin' in there! You can't make me, and I'm not goin'!" yelled a dark haired boy of around Rory's age.

A man presumed to be the kid's father dragged him by the straps of his bag towards the school.

"Wow. He's really glad to be here," Lorelai muttered sarcastically.

Rory peered around her mother at the scene just as the rambunctious kid slipped out of his back pack with plans to run. The man with him just hauled him back by the arm and told him no, even as the contents of the boy's bag spilled out onto the pathway. It was instinct for Rory to rush over and help, especially when she saw precious books tumble to the ground. Lorelai went after her daughter and between the two of them they picked up every fallen item.

"Jess, stop!" the man hauling the kid around said firmly, practically tossing the boy onto his feet right in front of Rory.

For the first time since the Gilmores saw him, he stopped moving and yelling both. The kid who was apparently named Jess just stood and stared a long moment at Rory. She got back to her feet, dusted off the three books in her arms then held them out to him.

"Hi," she said as she did so.

"Hi," he responded in kind, taking the books from her.

Lorelai looked over at them with a little amusement when they said nothing else.

"Hi," she threw in herself looking first at Jess and then at what she presumed to be his father. "I'm Lorelai Gilmore, this is my daughter Rory," she introduced. "We're new in town."

"Luke Danes," the mystery guy said shortly, taking the dropped back pack from Lorelai's hands and stuffing the contents back into it. "I run the diner in town. This is my nephew, Jess. He's new around here too, just recently came to stay with me for a while."

"Oh, that's nice," she nodded. "It is nice, isn't it?" she checked, actually starting to wonder.

Maybe Jess' parents had died or something awful like that. Something must've made him so angry and rowdy, Lorelai thought. Rory was never so badly behaved, not even coming down off an epic sugar high!

"It's... fine," said Luke awkwardly, then casting his eyes to Jess and Rory who still stood staring at each other.

"You read a lot?" he heard the little girl ask.

"Some," Jess shrugged, pushing his unruly hair back off his face. "You?"

"Yeah, some. A lot," she corrected with a smile.

"Me too," he admitted then, returning the expression.

"Well, isn't that something," Lorelai said, turning her attention from the kids back to Luke. "Two happy little literati we got here."

She wasn't sure what was going on with this Jess kid, and honestly, her introduction to his bad behaviour didn't thrill her, but maybe he just had it rough. If he liked to read and had the potential to be a good student like her Rory, that was a good thing. Besides, Uncle Luke was kind of hot...

"Which grade you in?" asked Jess then.

"Sixth," Rory answered immediately. "You?"

"Same," he agreed.

A minute later, Jess was grabbing his bag from Luke, zipping it up tight, saying goodbye and moving away. He and Rory headed for the steps, and Lorelai was just going to yell to her daughter, asking where her goodbye kiss was, when suddenly Rory came pelting back to her. She reached up until Lorelai leant over a little and then kissed her cheek.

"Bye Mom," she smiled, before rushing away again.

Luke looked at Jess a moment and the kid looked back.

"See ya, Uncle Luke," the boy gave a half-hearted wave.

"See ya later, kid," he smiled a little. "Have a good day!" he added as an after-thought.

Jess didn't mind so much. Uncle Luke wasn't so bad, this he told Rory as they headed up the into the school.

"So, where's your Mom and Dad?" asked Rory curiously. "I mean, my parents were never married," she went on to explain fast, just in case Jess thought she was about to judge. "I see my Dad sometimes, but I live with my Mom. We're best friends."

"I don't know my Dad," Jess shook his head. "And my Mom... She didn't want me around anymore."

"Oh," said Rory, not knowing what else she was supposed to say really. "Well, at least you have your uncle. I'll bet he's glad you're here," she smiled sweetly.

Jess just shrugged non-comittally and kept walking. They headed for the classroom where a kindly teacher waited to greet them. She seemed pleased to see her two new students, both starting just one term after the rest.

"Now you must be Lorelai Gilmore and Jess Mariano," she smiled down at them.

"Yes, ma'am," Rory replied with a nod. "Except, most people call me Rory."

The teacher, identifying herself as Miss James, seemed totally fine with the nickname and ushered her two new students into the classroom. She talked to them about the school and their schedules, as the rest of the class filed in and took their usual seats. Neither Jess nor Rory turned around until Miss James told them they should.

"Now, Rory, how would you like to take a seat next to Lane?" she pointed, and the small Korean girl half way down the room raised her hand to assist. "And Jess..."

Miss James didn't get a chance to offer him a seat, just watched dumb-struck as he followed Rory and sat himself in the seat on the other side of the aisle without a word. It didn't matter. He was sat in a previously empty seat and hadn't made a fuss. Miss James decided just to let him be.

The lesson began with a long explanation about the book they would be reading this term, and the teacher had Rory's rapt attention for a while, until a ball of paper landed on the desk in front of her. It could only have been Jess who tossed it there. Opening the paper in her lap so as not to be spotted, Rory read the words scrawled in pencil on the page.

_You want to come to Uncle Luke's diner after school?_

Rory smiled, looked at Lane, then to Jess, and finally back to the teacher. It was nice to make new friends so fast. She liked Stars Hollow already. Still, she was mindful of getting herself into trouble by passing notes. She watched Jess until he looked her way and then nodded her response to his question. He smiled so wide just knowing she was agreeing to be his friend, Rory had a feeling it was more than that. They were going to be the very best of friends, forever. She just knew it.

_To Be Continued..._


	2. Chapter 1 - Friends Like These

**A/N: I hope I have more readers than I have reviewers... though of course I do appreciate those people who did leave a review - thank you very much. Since this will be my first 'full length' Gilmore Girls fic, I am a little nervous about it. Hopefully this first proper chapter will show how relationships sit in this AU I've come up with, and then we can get into the important business of the story moving forward in some real way :)**

_**(For disclaimer, etc. - see chapter 1)**_

Chapter 1 - Friends Like These

"Emergency! Emergency!" Lorelai was bellowing as she rushed full-pelt into Luke's diner.

Nobody even flinched as she barrelled towards the counter and threw herself on a stool. Luke calmly stepped forward, placed an over-sized cup in front of his friend, and filled it to the brim with strong coffee from a specially marked pot. Lorelai dived straight in without a word, gulping down half the cup with ease. Luke watched her a moment, waiting for her to surface.

"You're my hero," she gasped, grinning up at him then.

"If I had a nickel for every time I heard that from you," he rolled his eyes, topping up her cup with a smile he couldn't quite help.

Lorelai giggled like a teen as she watched him get back to work serving his other customers. She loved Luke, not in any kind of romantic way, because that would be weird, but still. He was pretty much her best friend, except for Sookie. If a person could have two best friends, then they were hers, Lorelai thought, and she knew you could definitely have two besties, because her daughter did too. Speaking of which, Jess appeared as if on cue, smiling when he saw Lorelai sat by the counter,

"That time already, huh?" he checked, nodding towards her cup.

"Hey, didn't I teach you anything?" she gasped, wide-eyed. "Any time is a time for coffee!"

"I remember," he agreed with a single nod, still grinning. "Is Rory up yet?"

"That would be a negative, soldier," she teased him as she took in the army jacket he seemed to have taken to wearing lately. "We had Lane at our place last night," she went on to explain when he wouldn't give her the satisfaction of reacting to her joke. "Mrs Kim had an antique event thingy? I don't know," she waved her arm in some random gesture. "Anyway, it turned into kind of a slumber party at ours. I swear they were still talking at two a.m.," she complained.

"Don't tell me you can't take the pace anymore, Lorelai," Jess teased her right back. "I thought you were still 'one of the girls'."

"Hey, I'm as much one of the girls as you are!" she retorted, replaying that in her head a second later and realising how wrong it sounded. "Oh, I need more coffee," she groaned.

"Hey, Uncle Luke?" Jess called across to him. "More caffeine, stat," he said, pointing towards Lorelai. "I'm headed out," he added then, walking out of the diner and down the street.

Maybe it was kind of early on a Saturday for most teens to be up, but Jess had places to be, people to see. He and Rory had a project to work on for school, and the sooner they got started, the sooner they'd be done. Besides, he was doing Lane a favour by going over there too. He knew both girls well enough after all these years to be sure they'd have been experimenting with make up last night, maybe hair styles too. If they didn't get Lane back to normal before Mrs Kim came home there would be hell to pay. Nobody wanted the poor girl to suffer any more than she had to.

Headed up to the front door, Jess lifted up the turtle on the porch and retrieved the emergency key, letting himself into the Gilmore house. They never minded when he did that, Lorelai had said years ago that both Jess and Luke were always welcome to let themselves in if nobody was home. Obviously on this occasion Rory was actually inside, and Lane too, but no amount of knocking would get them to come to the door at this hour after too little sleep, he was sure.

Jess crept into the kitchen and put on the coffee pot. It was only then he realised why Lorelai had been so desperate in getting to Luke's place - the machine wasn't working. Frowning a little, Jess shed his jacket and thought about where to start in fixing the appliance. Finding tools in the Gilmore house would seem impossible to anyone else, but Uncle Luke had been keeping an emergency box in the place since Jess and Rory were kids, just for these kind of jobs. Straight into the closet under the stairs, he laid his hand on the box immediately. A screwdriver and a little ingenuity, he was bound to find the loose wire or whatever, get the machine fixed, and have hot coffee waiting before he ever woke the girls up.

It was a solid plan, and it probably would've worked too, except for the part where Jess completed his task, and stepped backwards onto his own jacket that had fallen from the chair to the floor. He skidded, tried to right himself, missed, and crashed to the ground.

Rory's bedroom door flew open as Jess scrambled back to his feet. There framed in the doorway was a sleep-rumpled Miss Gilmore with a soft toy chicken held over her head like a deadly weapon. Lane hovered behind her, looking completely terrified. Jess would've laughed if he wasn't so sorry to have genuinely scared them.

"Oh my God, Jess!" Rory exclaimed at the sight of him. "What were you even doing?!"

"Fixing your coffee machine... and breaking a couple of limbs in the process," he admitted, checking his elbow and knee both as they throbbed the moment he stood up. "You're welcome, by the way."

"Oh God, what time is it? Is it late?" said Lane, starting to panic.

"Relax, it's still early," Jess assured her. "Plenty of time to... fix things," he said awkwardly as he noticed the crimped patches in Lane's hair, and the copious amounts of make up she was wearing.

Rory didn't really go for a lot of paint on her face. In Jess' opinion that was a good thing since she really didn't need it. Still, she was allowed what girls called essentials. Lane was not permitted any make up, hair colour, not even perfume because her mother was just that crazy, or so Jess thought. Either way, it looked as if Lane had made up for the lack of girly extras in a big way last night. Ms Kim would hit not just the ceiling but the moon and beyond if she saw her daughter right now.

"Are you okay?" asked Rory suddenly as she came into the kitchen, all bare foot and pyjamas. "Jess, you're bleeding!" she said worriedly, taking a hold of his arm.

There was in fact blood leaking through his shirt sleeve, and Jess swore under his breath as he pulled back said sleeve and surveyed the damage.

"Nah, it's nothin'," he assured her. "Just a scratch, no big deal... You are not sticking one of your girly pink band aids on me!" he insisted just the moment he realised that Rory was headed for the first aid box.

"Hello! Can we concentrate on the more important injuries here!" Lane insisted. "Like the ones I'm going to get if Mrs Kim sees me like this!" she said in a rush, gesturing to her general appearance.

"Bathroom," Jess instructed, pointing upstairs. "Wash your hair, wash your face," he told her calmly, glad when she didn't argue and just went already. "Rory'll be up in a second!" he called behind her, yanking his arm away when he realised Rory was right now trying to do just exactly what he told her not to with a bright pink sticking plaster. "Seriously?"

"Yes, seriously," she insisted. "You're not bleeding to death in my kitchen, okay, Rocky?" she said firmly, sticking the Barbie band aid onto his elbow where the scrape was.

Jess rolled his eyes and pushed his sleeve back down.

"And just think, if I hadn't been such big brave girl, I might not've got the really good bandage."

"That is true," Rory retorted, sticking out her tongue as she headed back to her room. "Thank you for fixing the coffee machine!" she called over her shoulder, before pushing the door almost closed whilst she got dressed.

It didn't bother her that Jess saw her so under-dressed. He saw her in pyjamas before and she'd him in similar attire. They had been best friends from age eleven, it just didn't seem weird. There was still no way she was getting naked in front of him, because that was just... Rory couldn't even think about that!

Trading her sleepwear for a fresh new outfit from the closet, Rory heard Jess ask if she wanted food with her coffee. He retracted the offer before she could answer when he realised there was nothing edible in the fridge, as usual.

"I should've brought something from the diner," he said, almost literally face-palming as Rory came out of her room, pulling her top down to meet her pants.

"It's fine," she assured him. "Mostly I need the coffee. We can eat later when Lane is all cleaned up and home again. Snacks and studying go together like Bogart and Bacall," she grinned, rushing right through the kitchen, down the hall, and up the stairs calling Lane's name.

Jess watched her go and shook his head. Rory was the only person he ever met who knew as much about old movies, classic books, and genuinely decent music as he did. Well, Lorelai was pretty good too, but that was different. A lot of older people knew that stuff, not many as young as Jess and Rory did. Lane was cool, way cooler than she seemed, but she still wasn't quite the same to Jess as Rory was. As sappy as it sounded, she really was his best friend, and he wouldn't know how to get along without her these days.

Shaking his head free of such stupid, mushy thoughts, Jess grabbed three mugs from the cabinet and poured out the coffee. It wasn't long before Rory and Lane returned, the former taking a seat whilst the latter crashed into the bedroom to get properly dressed.

"Being Mrs Kim's daughter must be so exhausting," said Rory sadly as she picked up her coffee and took a long drink, a pleasured kind of moan escaping her throat.

Jess tried not to notice as he sat down on the other side of the table and picked up his own drink. He never knew women who loved coffee as much as the Gilmore girls. He was pretty sure he never saw anything as sexy as Rory with her first cup of the day either, but that was the kind of thoughts he put down to over-active hormones and chose to ignore. Rory was Rory, not sexy, and not someone he was going to date, because that would be ridiculous. More ridiculous than Mrs Kim being happy about her daughter covered in make up!

"Okay, I think I'm done. Am I done?" asked Lane worriedly when she appeared in front of her friends again.

She performed an awkward, paced out twirl, and both Rory and Jess inspected her appearance. As far as they could tell she was fine, and they said as much completely in unison, making themselves laugh. It happened a lot, to the point where they'd stopped saying the whole 'jinx' thing years ago, when they still considered themselves kids. Now, at fifteen and sixteen, Rory and Jess were young adults, but still the same good friends they'd always been.

"Bye, Lane!" they both called as their friend ran for the front door and it slammed behind her as she exited the house and hurried home.

"Poor Lane," Rory sighed then, leaning her chin in her hand and her elbow on the table. "I wish her Mom went easier on her."

"We can't all have great Moms like Lorelai," said Jess, looking down into his coffee.

So often he was just overtly cool and calm. Rory often forgot how broken he was inside. Jess' parents didn't want him. His Dad had split when he was just a baby, and then at age eleven he'd been shipped off to his Uncle Luke. He claimed he was okay about his Mom, Liz, letting him go, never wanting him back. It wasn't her fault she couldn't cope. Still, Rory knew it hurt him to have been sent away like that, it had to. People could cope without a Dad in their life all the time, Rory knew, because she only saw Christopher a handful of times a year. It was a mother she figured everyone needed, and should have if they possibly could.

She recalled a time way back, the first Mother's Day since she met Jess, telling him he was quite welcome to share Lorelai with her. From that day on, he always brought her flowers on the day, and she accepted them with grace and gratitude.

"What?" asked Jess when he looked up then and found Rory staring at him strangely.

"I was just thinking," she shrugged.

"Yeah, well, you think too much sometimes," he warned her, moving to pick up her mug and his for refilling purposes.

"Said Rodin's famous sculpture," she teased him. "There are times I swear the cogs are turning so fast in your head I can hear them across the room!"

Jess smiled but said nothing, just handed her the refilled cup and dropped back into his seat. This was just how they were, all banter and teasing most of the time. They knew each other so well. He and Rory rarely fought, and when they did it was something and nothing. They always made up by the end of the day, following the rules Uncle Luke liked to preach that you should never let the sun set on an argument. As far as Jess knew from other sources, that was mostly to be applied to married couples making up before they went to bed together. He never did tell Rory when he realised it, it'd be too weird to compare the two of them to a couple somehow. It wasn't that they were brother and sister either. Their relationship was more than a simple friendship after all they had gone through together, all they had helped each other cope with and achieve. Still, Jess wouldn't like to try and put a label on it. He didn't usually feel the need to.

"So, history project," he said eventually, drumming the table and pulling his books across in front of him. "You ready to do this?"

"I think so," Rory nodded easily. "Let's get started."

* * *

"Rory!" Lorelai called as she came into the house.

Though it was Saturday, she was needed at the inn this morning and one incident after another had kept her there well into the afternoon. She had called her daughter to let her know she would be longer than planned, but still felt bad for not being around on the weekend to see her girl.

"In here, Mom!" Rory called back, laughter in her voice that Lorelai well understood as she came into the living room and saw Blazing Saddles playing on the TV.

"So much for studying, huh, kids?" she said, leaning over the back of the couch.

"We did the project first, _Mom_," Jess rolled his eyes, earning a playful smack upside the head for his trouble.

"And that is very commendable, young Mariano," she said definitely. "But your crime was not pleasure before business," she told him definitely. "It was starting the movie without me!"

Rory immediately flipped off the video and started rewinding the tape.

"We were only a few minutes in, we can start over," she said definitely.

Lorelai immediately melted at how sweet her kid really was.

"I raised you right," she said as she dumped her jacket and purse in the chair.

"I'll get you a drink," Jess told her, jumping up and heading for the kitchen.

"I helped raise you right too," she added as she watched him go. "Thanks, Jess!"

Lorelai dropped down into the middle of the couch beside Rory. Without a word, she pulled her into a hug and kissed the top of her head.

"You have a rough day, Mom?" Rory checked.

"It was loooong," Lorelai over-emphasised. "You?"

"Pretty good. Lane got home on time, her Mom never even knew there had been any products by Messrs. Maybelline or Max Factor on her face," she smiled. "Jess and me got our project done, no sweat, and now, movie on, pizza on the way, jelly beans in the meantime," she explained succinctly, and also at a mile a minute, as was the Gilmore way.

"Sounds good to me," Lorelai smiled, not at all phased by how long she had left two teens alone in the house.

Rory was just the most responsible kid, always had been. Lorelai meant what she said about rising her right. As for Jess, he still had his moments, but the rowdy kid that had arrived in Stars Hollow five years ago had certainly matured and mellowed some over time, thanks in no small part to Luke, Lorelai, and Rory as well. They were the family he needed, the love that he craved, though he never would admit that, Lorelai was sure. He turned out pretty good, and he and Rory were just such good friends. Lorelai never worried about him being a boy in her house. She never felt she had to be concerned about anything happening between Rory and Jess other than study, jokes, and the like. Best friends, that was all they were, even after the teen years hit, and Lorelai was pretty happy about that if she was honest.

"Here you go," said Jess then as he returned with Lorelai's drink, as promised.

"Thanks, hon," she smiled, taking the glass from him and drinking down a big gulp. "Okay," she said then, putting the glass on the table and flinging her arms along the back of the couch behind both Rory and Jess. "Movie time!"

Blazing Saddles was duly switched back on and began again from the opening credits. The three on the couch sat back, ready for laughter, silliness, and fun. Maybe they were an odd set of people with some relationships going on that they couldn't really explain, but that didn't matter to them. They were happy as they were, and all hoped that wouldn't change any time soon.

_To Be Continued..._

**A/N2: Honk if you love Rory & Jess in this story! ;) Sorry, I just re-watched the episode where Lorelai was talking about 'honking' bumper stickers! lol But seriously, please let me know in a review if you like what I have going here :)**


	3. Chapter 2 - Old Habits, New Beginnings

**A/N: Thank you to everyone who left me feedback in any form because I really appreciate it :) I love the concept I have going here and its good to know I'm not the only one! So, see how this chapter grabs ya! ;)**

_**(For disclaimer, etc. - see Prologue)**_

Chapter 2 - Old Habits, New Beginnings

Most kids didn't like Mondays. Jess didn't mind them so much, in fact he kind of liked them. He kind of liked Stars Hollow too, though he never expected to when he was first sent here to live with his Uncle Luke. Seriously, he considered, no child of eleven wanted to be taken away from their home, their school, their friends, and thrust into a whole new world. Coming from the big city life of New York to this little back water town, it was too strange, and it always felt like every eye in the place was on him. Jess hated that, at least in the beginning anyway.

Growing up as Rory Gilmore's best friend, now that made all the difference. She was quiet and studious when they met, in class anyway. Away from her books, she was a little crazy and strangely into an awful lot of the same things Jess was himself. They would hang out at the diner, and Lorelai and Luke would talk, bemoaning the trials of raising kids, always in a playful teasing way, whilst Jess and Rory did their homework or read together or something. Yeah, growing up here had turned out better than Jess ever could've imagined things going for him in New York. His mother wasn't all bad, but Liz just wasn't cut out for parenthood, even Luke had been heard to say so. The fact was, nobody really thought he would be good Dad material either, especially Jess, but he was wrong. Sure, they had their moments, their fights and all, but most of the time they got along.

People said that Stars Hollow was good for Jess, and Lorelai had even said once or twice that Jess was good for the town. She thought the place needed a little more life in it, and between the Gilmores and him, Jess supposed that's what they gave it. He didn't know he was smiling like an idiot, or continuously wiping the same cup on the dishtowel for the last ten minutes, until Luke told him so. The moment his uncle spoke, Jess started, almost dropping the cup. He saved it from smashing on the counter by the nearest of margins.

"What were trying to do? Give me a seizure or somethin'?" he asked snippily.

"Geez, how was I supposed to know you were asleep standing up," Luke grumbled. "I need you to move, you're blocking the register," he explained the, gesturing for Jess to move his behind already.

With an eye-roll, the teenager moved over, and put the now very dry cup onto the shelf. He shouldn't be standing around day-dreaming like a girl and he knew it. There was still almost an hour before he needed to be in school, and he really wanted to finish reading that book before he had to go meet Rory and Lane. He was about to head for the stairs, when Luke cut by him and said he'd be back in a second, rushing up to the apartment himself. Jess sighed, knowing he was supposed to man the counter until his uncle got back. He stopped caring when the door bell chimed and Rory came rushing in faster than he'd ever seen her run in his life.

"Jess!" she gasped in oxygen as she pelted towards the counter and landed with a bump against it.

"Hey, where's the fire?" he asked with a smirk he couldn't help.

"Right here in my hand!" she told him, literally laughing as she forced a piece of paper into his hands. "Read, read!" she encouraged,

"Alright, alright, I'm reading!" he told her, gesturing for her to stop bouncing. "Take your Ritalin!"

Jess was smiling at her enthusiasm, even if he didn't understand it, and started to focus on the letter she had handed to him. His happy expression soon faded into a genuine frown when he realised what he was looking at.

"You got into Chilton," he said flatly, and needlessly too, since that much was already extremely clear to Rory, hence the Tigger-like bouncing.

"I did, I got in!" she jumped around some more, looking like a bug on a hotplate. "Isn't that great?"

When Jess remained silent and stoic too long, Rory stopped bouncing. She visibly deflated like a balloon with all the air gone out of it. Jess failed to notice as his eyes scanned the letter over and over. Rory was going to Chilton, in Hartford, away from Stars Hollow where he would be, without her. There was suddenly a lead weight in his stomach and it felt as if the floor went out from under his feet.

"You're not happy for me," she said then, a statement not a question.

Rory was disappointed, that much was clear, and Jess felt awful the moment he glanced up and realised he had caused her pain. That was the last thing he ever wanted but this had floored him. Of course he knew Lorelai had been trying to get Rory into Chilton, and he never doubted that she was smart enough to pass the tests. There was a money issue but he was sure that had been figured out already. He'd just been in denial, Jess supposed. He never wanted the day to come when he didn't have Rory there with him in school and everything.

"I'm sorry," he shook his head and got himself out of a daze. "Of course I'm happy for you, this is great!" he told her, trying to sound enthusiastic when it was in fact the last thing he felt.

"I've known you too long, Jess," she said, with an expression that he knew so well. "That 'it's great' was more fake than Pamela Lee. What's wrong?" she asked, as she took the letter back from him.

"I don't know," he shrugged, but her so-called withering stare didn't let up, and he knew he wasn't getting away with that bull, not with a Gilmore. "I just... I guess, I'm just gonna miss you, okay?" he admitted, concentrating more on wiping down the counter than anything else.

Rory smiled at that. It was so sweet that he would miss her, but Jess would hate it so much if she said so. He tried to be so cool, so tough, especially as they got older and into their teen years. Rory learnt to keep her lip buttoned if she was ever tempted to say he was cute, sweet, or adorable at all. It just made him so mad, and not even in the funny way.

"It's not like we'll never see each other," she told him seriously, putting her hand on his arm to get his attention back. "I'll come to the diner for breakfast, and then there's after school, weekends, special days. This town is so small, you couldn't avoid me if you wanted to."

"Like I'd ever want to," he said, rolling his eyes, that familiar smirk on his lips that made Rory smile all over again.

She would never want to hurt Jess. He was her very best friend, and of course it was sad that they wouldn't be attending school together anymore. He and Lane had been there since Rory was eleven, always either beside her in class or catching up at lunch. It would be weird not studying the same things at the same time in the same place, but this was such a big opportunity. Chilton meant Harvard was an easier goal, it meant so much to Rory. Still, her friends meant so much too.

"So, you can be happy for me now, right?" she checked with Jess, glad that he had least looked like he was trying to smile at this point.

"Yeah, I guess," he told her, trying to shake off the shock and the sadness that had hit him way harder than he expected. "You did good, Gilmore."

"You better believe it, Mariano," she grinned widely, even as she started backing up towards the door. "I gotta go tell Lane about this, but I'll see you later, okay?"

"Okay," he agreed with a nod, and then she was gone, the door slamming and bell ringing loudly in her wake.

Jess let out a long breath he hardly knew he'd been holding. Was he happy for Rory in achieving a goal she so wanted? Yes, of course, he was. Was he genuinely happy to know she would be in his life any less than she was now? No, not at all. He felt sick.

* * *

Lorelai hung up the phone and sank down onto the couch with no breath left in her body. This was horrible, genuinely horrible. Finally Rory's dreams were coming true, the dreams Lorelai had herself for Rory too, and yet in came the anvil like always to squash them flat just when things were going good. Chilton had accepted Rory and that was great, but now they wanted tuition fees, upfront no less. Lorelai just didn't have the money, not now all out of the blue. Her mind raced with ways to get said cash, everything from the sensible to the insane. Unfortunately, it was some of the crazier plans that actually seemed to be her only viable option.

There were two really obvious answers to the question 'where the heck do I get a few thousand bucks?' and Lorelai didn't want to face either of them. Her first option was Luke, and bile rose in Lorelai's throat just considering asking him for money. He was her best friend, had been for years now. With her daughter and his nephew practically living in each other's pockets since they were eleven, they were always going to be close. Plus Luke ran the diner where Lorelai got the best coffee she ever tasted, and he was always on hand when she needed a man around the house. They just got along, no more, no less. Asking him for a favour was fine, but money? It would ruin a perfectly good relationship they had spent five years carefully building and she just couldn't stand it.

Option two for Lorelai was to face her rich parents and ask them for the cash. In their case, there really wasn't a relationship to ruin. It had been pre-broken by Lorelai's getting pregnant and running out at the age of sixteen, so it was actually the better of her two choices. That didn't mean she actually wanted to go down the road of asking.

Rory had left about a half hour ago to tell Jess and Lane her good news. She was bounding like Tigger and smiling so wide, Lorelai was surprised her face didn't split in two with the pressure! There was no possible way to take that away from her. What kind of mother could bear to? Certainly not Lorelai that was for sure.

Taking a deep breath, she began dialling her parents' number, then stopped short of the last digit and shut off the phone. She didn't want Rory coming in and hearing her begging money from her parents, and it seemed worse somehow not to be face to face with them when she did this. No, Lorelai had to go see her Mom and Dad and get this figured out. In exactly one week, Rory would be starting Chilton. Despite the panic and pain inside, Lorelai had to smile about that.

* * *

Luke watched Jess collecting empty plates and glasses from the tables like the kid was on another planet. He just wasn't paying attention, as evidenced by the way he took away Kirk's sandwich whilst he still had half of it left to eat! Something was up, it had been since Jess got home from school. Actually, he wasn't right before school either. Luke had one idea as to why, but somehow he didn't think bringing it up was going to help. It was only when Jess turned too fast and knocked three empty glasses flying off the counter onto the tile, Luke felt he had to speak up.

"What is up with you today?" he asked, deliberately drowning out Jess' own cussing under his breath before the customers heard.

"Nothin'," his nephew grumbled, pulling the brush from Luke's hands and sweeping up the mess he had made himself.

Unfortunately it seemed Luke had no choice but to broach the subject of what was bothering Jess. The touchy feely stuff really wasn't his area, and usually he'd ask Lorelai to step in. When the topic for discussion was probably going to be Rory, that didn't seem to be appropriate somehow.

"Jess, c'mon," he said quietly, leaning over the counter. "Is this about Rory going to Chilton?"

"No!" his nephew immediately snapped, moderating his tone when he realised he was getting a little too much attention. "I'm not pathetic, okay?" he confirmed, pushing the broom back into Luke's hands and turning to stalk away.

"Nobody thinks you're pathetic, Jess," his uncle assured him as he followed him towards the stairs. "She's your friend and she's not gonna be around as much anymore. It's natural that you're gonna miss her."

Jess stopped in the doorway but didn't turn back. He hated this. He hated that he felt this way over some girl. Of course, Rory wasn't just some girl. She was his best friend, and more than that... Even thinking it was crazy.

"I've got homework to do," he said as he trudged up the stairs.

Luke watched him go with a sigh. Teenagers. They were more trouble than they were worth sometimes. It could've been worse and he knew it. Having Jess here from the age of eleven had given him a chance to mould the tearaway into a decent sort of young man. Lorelai had helped a lot too.

"Hey," she said as she entered the diner, and Luke couldn't help the odd smile that quirked his lips when he turned t face her. "What?" she asked, wondering what the look on his face was all about.

"Nothing, I was just... It's nothing," he assured her, literally waving the moment away.

"You sure?" Lorelai checked, as she took a seat at the counter and looked down at the smashed glass beyond.

"Yeah, it's just... Jess had an accident," he explained, clearing up the broken shards. "He's feeling a little... I don't know. With Rory going away to another school, I just think he's feeling a little abandoned or jealous or something?" he tried, not really sure he was explaining it at all well. "Honestly? I don't know what to say to him."

Luke went out back to dispose of the broken glass and wash up, whilst Lorelai watched him go and then turned her gaze to the stairs up which Jess had probably gone.

"Poor guy," she said more to herself than anyone else. "Like he needs any more abandonment issues. But y'know Rory's not the type to forget her friends just because she's going to Chilton," she told Luke as he returned to her, pouring a cup of coffee in front of her on automatic.

"Oh, I know, and Jess knows it too," he nodded in agreement. "We're really happy for her, both of us, he's just... he's a teenager."

"They are a fickle bunch," Lorelai agreed, thanking Luke for her coffee and taking a long drink.

"So, you wanna order?" he checked, watching her shake her head in the negative.

After she swallowed her mouthful and replaced her cup on the counter, she looked up and answered properly.

"Actually, I'm waiting for Rory..." she paused when the bell over the door rang, looking back to see her daughter entering. "And as if by magic! Hiya, hon!" she grinned.

"Hey," Rory smiled back, moving towards a table as her mother joined her. "Hey, Luke," she waved to him.

"Hey, Rory. Congratulations on Chilton," he told her with a genuine smile. "You did good."

"Thanks," she almost blushed at the compliment, tucking her hair behind her ear in a nervous habit.

Luke was a great guy and a real friend to both her and her Mom, but Rory knew his compliments were few and far between. That was why they were all the more special when she earnt one, and she really appreciated it. Chilton was a big deal, and she was just so excited about it. Her Mom had been excited, this morning anyway, though right now she suddenly looked too serious.

"What's going on?" asked Rory with a frown, just as soon as Luke walked away. "Something is, I can tell," she insisted, when it seemed that Lorelai might try to squirm out of explaining.

"I, er... I saw your grandparents today," she started to explain, and Rory listened with mostly rapt attention to what came next.

Something didn't add up. It made no sense that her Mom had gone to see Grandma and Grandpa all out of the blue. It certainly seemed weird that after years of only seeing her grandparents on holidays and special occasions, suddenly Rory would be going over to their house every Friday night for the foreseeable.

"So, are you okay with that?" asked Lorelai, looking almost worried she wouldn't be.

"Sure, I guess," Rory shrugged. "I mean, I love Grandma and Grandpa, it'll be nice to see them more."

"Yeah, it will," her mother agreed, not looking entirely convincing. "And once this Friday night is over, we can spend the whole weekend in celebration mode!" she said, with genuine excitement then. "I cleared my schedule, no work at the inn, nothing but spending time with you, movies, junk food, and obviously Jess is invited."

"Obviously," Rory rolled her eyes like it was a ridiculous idea that her best friend would not be a part of their Chilton celebrations.

It sure would be weird not attending Stars Hollow High anymore, but Rory meant what she said to Jess, and to Lane as well, about still spending lots of time with them outside of school hours. Life was changing, and that was kind of scary, but at the same time it was exciting. Rory Gilmore was going to Chilton, and she just couldn't stop smiling about it!

_To Be Continued..._


	4. Chapter 3 - Night Before, Morning After

**A/N: I'm amazed but thrilled to have readers, and more so reviewers, for this fic. I am so incredibly late to the party on the whole Gilmore Girls fandom, so it genuinely makes me giddy that people are reading and leaving feedback, seriously, you're awesome people! Now, parts of this chapter may not be popular, but bare with me, folks, because it'll be worth it, I swear :)**

_**(For disclaimer, etc. - see prologue)**_

Chapter 3 - The Night Before, The Morning After

The week had passed in a blur for Rory Gilmore. Once the news came that she was accepted for Chilton, there was really no need for her to attend classes at Stars Hollow High anymore. She still had to drop in a few times - see the principal, clear out her locker. It seemed weird being there without actually _being there_. Jess and Lane were still attending class and she passed them in the hall a couple of times, as well as a few of her other friends. It hit Rory just yesterday that she was never coming back here as she piled her books and papers into her arms for the final time and stepped out through the doors. This wasn't her school anymore, she didn't belong here. She was a Chilton girl now, and Rory felt the strangest mixture of happy and sad about it. It was the end of something but also an awesome new beginning. That part made Rory practically giddy with joy, as did thoughts of this weekend.

Last night had been a little odd, seeing her grandparents in such unusual circumstances. Most of the time it had to be Thanksgiving, Christmas, or some other specific holiday or occasion before she saw them, barely even once a year. Now they were going to be headed over there every Friday, and Rory couldn't get her Mom to explain that one. There was something going on, and doubtless she would find out eventually. As it was, the dinner went okay, a little frosty in places maybe, but nothing too terrible.

Today, Rory had made time for Lane. There was no way she would be allowed to stay over at the Gilmore house on a Saturday night or even leave her home on Sunday unless it was for church, so today had been a girly Rory and Lane day. After her friend went home, Rory headed to the book store to pick up the last few things she needed for the Chilton reading list. She was later than she meant to be as she hurried home for a movie marathon and junk food binge with her Mom and Jess. Just a couple of streets from her house, Rory started flagging. She really had too many books in her bag and ought to have known it long before she tried to hoist said bag higher on her shoulder, only for the strap to snap in two.

"Oh! Stupid thing!" she exclaimed as the bag gave way and her books went tumbling all over the sidewalk.

Rory hadn't a clue how she was going to carry all the books without the bag that was now of no use. Still, she crouched down and tried to tidy them into a pile at least.

"Need some help?"

A voice behind her was startling, and Rory turned quickly to see a young man approaching that was vaguely familiar. He was almost ridiculously tall, and kind of hot actually.

"Oh, um... thanks," she muttered as he stooped to help pick up her fallen books for her. "The strap just completely gave way," she explained, showing him her bag as they made fast work of collecting up her fallen purchases.

"And you were trying to carry half the bookstore home?" he smiled, all pearly teeth and boyish charm.

Rory's heart skipped a beat.

"Something like that," she smiled on back at him. "Um, I'm sorry, I don't even know your name," she admitted then, sure she recognised him from somewhere but not really knowing why.

"Dean," he told her, looking like he might've put out a hand for her to shake if he wasn't already holding so many books. "My family just moved here from Chicago. I saw you around Stars Hollow High. You're Laurie, right?"

"Rory, but close," she corrected, looking at the books in her arms and then the ones Dean was holding.

Honestly, she really wasn't sure how she was going to take those from him and make it home. If they were just a little closer she would have left some on the sidewalk and made two trips, but as it was, she didn't really want to look that dumb, not in front of Dean.

"I can walk you home, if you want?" he offered, as if he had read her mind, or maybe he just saw her pained expression.

"Um, yeah. Sure, why not?" she replied awkwardly. "Thank you," she added like an after-thought.

'_God, I am so bad at this!'_ Rory thought, wincing at her own inability to form a sentence in front of the guy just because he was so cute. Liking boys from afar, that was what she was good at. She and Lane would go googly eyed over some guy they were likely never to meet, pop stars and movie stars, even guys in school that would never give them the time of day because they were just older, cooler, whatever. Rory had never had a date, never kissed a boy. She just knew she was blushing purely through thinking about such things and only hoped Dean wouldn't notice in the dark.

"So, I'm guessing you read a lot?" he asked suddenly, jolting her from her run away thoughts.

"A very lot," Rory agreed with a nod, "but some of these are for school. I'm transferring to Chilton, so new reading lists and all. Then when I got to the book store I just couldn't help myself," she laughed at herself, feeling so dumb still.

"Oh, you're leaving Stars Hollow High?" he checked, looking oddly sad about that as they reached Rory's house. "That's too bad, when we just met and everything," he smiled.

"Well, I'm sure I'll see you around town sometimes," she said, as she balanced books on her knee and unlocked the front door. "Next time I'm damselling, I'll be sure to call for you."

When she glanced at Dean he was smiling at her in such a way as to make her knees buckle. Rory forced a breath through her body and concentrated on going into the house, a task made harder by the load she was carrying, and the fact her hands were shaking too.

"Hey, Mom! I'm home!" she called when at last she got inside.

"Hi, hon," Lorelai smiled as she met her daughter in the hallway, "and friend," she added on seeing the tall boy behind Rory.

"This is Dean," she made introductions, as the pile of books Dean had been carrying was duly parked on the side table. "He helped when I had a crisis," explained Rory, showing her Mom the broken bag strap.

"Oh, damn!" her mother cursed, assessing the damage with a very similar frown. "You loved that book bag."

"I did," Rory agreed. "But time for new things, I guess," she said with a sudden smile and a definite look towards Dean, that he clearly wasn't supposed to see.

Lorelai bit her lip and tried not to react, especially since Dean was stood by the door, shifting awkwardly and looking between her and Rory. Somebody had a crush, and she honestly wasn't sure if it was her daughter or the new guy that was falling fastest.

"Hey, Lorelai," said Jess as he came through from the kitchen. "I changed the... water bottle," he said, his sentence becoming disjointed when he came across the three people in the hall that ought to have been two.

Lorelai watched Dean and Jess eye each other suspiciously. It was a little too The Good, The Bad, and The Ugly to be a good thing.

"This your brother?" asked the taller of the two.

"No, this is Jess," Rory giggled like the girlish waif she never was. "Jess, Dean," she introduced them.

Loreali never felt so awkward in her whole life, and that was really saying something. Jess folded his arms like he was readying for a rumble. Dean just made himself taller, in some feat of genius that Lorelai didn't understand at all, because it just shouldn't be possible.

There had never been a guy in Rory's life before, no-one but Jess, and whilst they were only ever friends and nothing more, it was clear he was feeling territorial here. Lorelai couldn't blame him for that, she just kind of wished that Rory would've noticed. She didn't.

"So, anyway," she said, looking to Dean. "We're kind of having a celebration, for the whole Chilton thing. If you're hungry and you like movies, you could stay, maybe?"

Lorelai winced at that. She didn't want this guy here, and the pained expression on Jess' face sure proved he didn't either. To be fair, Dean probably had lots of wonderful qualities, he sure was cute, even Lorelai could see that. The fact was, this was a night for Rory to spend with her Mom and her BFF. Sharing her with a third person was not an option, even if the whole concept was pretty selfish. Mostly, Lorelai just couldn't stand this atmosphere a moment longer!

"Oh, Rory. I'm sure Dean has a home to get to," she said diplomatically. "A family, homework, something like that, maybe all three?"

Dean opened his mouth to argue but that look on Rory's Mom's face was unmistakable. She wanted him out of the house, as did this Jess guy. Seemed Dean was leaving whether he liked it or not. He didn't like it.

"Er, yeah, I guess I should go," he said, turning to head out of the door.

"Good choice," Jess muttered, watching Dean go with a smirk he couldn't help.

He couldn't say why the guy bothered him exactly. They hadn't really met until now, though he had seen the new kid around school. He had blown in from the windy city, so they said. All Jess knew was that he was a jock, a pretty boy, and he was too damn tall. Now he was trying to get friendly with Rory, and that was definitely something Jess didn't like. He wasn't going to explain why even if he was asked, but that was just the way it was.

"So, Dean, huh?" said Loreali, putting her arm round Rory's shoulders and giving her a squeeze. "He's new."

"He is," she grinned too wide, "and super-cute. Don't you think he's super-cute?"

"He's not my type," said Jess, at which Rory only rolled her eyes and playfully slapped him across the shoulder.

When Rory headed into the living room, saying she had movies to pick out, Lorelai hung back in the hallway with a moody Jess.

"Hey. You okay there, slugger?" she checked, even as he stared towards the front door still, despite the fact Dean was long gone.

"Just peachy," he replied with the fakest smile ever and they both knew it.

Lorelai wasn't about to delve too deep into why he had such a big problem with the new guy, not here and now anyway. If there were reasons not to like Dean, real or otherwise, she and Jess were going to have to have a talk about that later. For now, they were here with a purpose, and that came first.

"C'mon," she told Jess, putting her hand to his back and giving him a gentle shove towards the living room. "'Cause this junk isn't going to eat itself."

* * *

Lorelai Gilmore was getting too old for sleeping on the floor. This she realised when she came to on Sunday morning with a crick in her neck and muscles screaming just about everywhere they could scream, plus a few more places besides. The TV was all grey fuzz, the coffee table was strewn with candy wrappers, empty bowls, and the like. Over by the couch, propped up by cushions and each other were Rory and Jess. Honestly, Lorelai couldn't help but smile as she noted how adorable they looked. Jess had his arm around Rory's shoulders and her head was rested on his chest. They were perfectly still and happy. It would be oddly romantic if they were a couple, and just entirely sweet if they were siblings. As they were best friends, Lorelai had to wonder how they would feel about waking up that way. She thought it best not to be the one to actually cause them to stir. Going forward, she often wondered how their relationship might change. She was always doubtful that a romance would ever occur after all these years of being BFF, and yet it wouldn't be awful if it happened, she supposed. Jess sure didn't like the idea of Rory liking Dean, which had to mean something.

"Less thinking, more coffee," she said softly to herself, levering her backside up off the carpet.

Lorelai bit her lip so as not to make yelping sounds of pain as she attempted to put one foot in front of the other. So much sugar had them high 'til midnight, but after that, the excesses of food had caught up to them, and the crash led to them all sleeping on the floor. Lorelai really had to learn to stop before they went that far, for the sake of her own ass if nothing else. Damn, she had some pins and needles in some places!

Back in the living room, Jess began to stir. He wasn't sure what had woken him until he let his eyes flicker open and realised Rory's hair had been tickling his nose. He didn't remember falling asleep. He sure didn't remember being in this position when it happened, but he didn't mind so much. Rory was soft and warm against him and she smelt amazing, just like always. Not that he thought about her _that_ way at all, he reminded himself, as he started disentangling his limbs from hers.

Rory gave a whimper at the movement and being woken up so abruptly. In her mind, her warm comfy pillow was moving and that just wasn't good enough. She gripped onto Jess' shirt a moment, until her eyes opened and she realised what was happening.

"Oh, hey," she said, feeling a little silly as she sat upright and rubbed her eyes with the back of her hand. "Um, what time is it?" she asked.

Jess stretched his arms above his head and looked up to see his watch.

"A little after nine," he told her, working the kinks out of his body as Rory did the same.

"Wow, we really laid waste last night," she noted as she cast her eyes over the mess of wrappers and packets on the table. "Mom?"

"Right here, baby," Lorelai replied as she walked through from the kitchen with a decidedly odd gait.

She didn't realise she was walking strangely until Rory and Jess gave her twin looks of confusion. Lorelai straightened up so her butt wasn't sticking out and removed her hands from it at the same time. Thankfully the muscles down there had woken up some now anyway.

"Coffee's on its way," she said with a smile as she moved to start clearing up the debris from the floor and coffee table.

"Is it weird that I'm still hungry?" asked Rory as Jess got to his feet and offered her a hand up.

"For you? No, not weird," he confirmed. "I never met a person... two people," he amended looking to Lorelai next, "that could eat like you do and not weigh three hundred pounds a piece."

"Well, we are special," said Lorelai cheerfully.

"We are that," Rory agreed with a nod. "So, what are we doing about lunch today? Luke's?" she checked.

"That's the plan," Jess told her, getting her attention back. "I'm supposed to take you over there around noon. Uncle Luke has this whole celebration, 'congratulations on Chilton' jamboree planned," he rolled her eyes. "It's not exactly going to be the biggest thing since Macy's Thanksgiving Day parade, but he wanted to do something."

"Aaaw, that's so sweet!" Rory enthused. "Mom, isn't that so sweet of Luke?" she called to her.

"Has oft been said, Luke Danes is a real sweetheart," she dead-panned as she returned to the room, the contents of her hands no longer bowls and packets, but something decidedly plaid in colouring, Jess noticed. "Rory, I got done hemming your Chilton skirt yesterday. You should go try it on, see if it needs anymore adjusting."

"Ooh, thanks, Mom," she smiled, kissing Lorelai's cheek as she rushed off to her room to change.

Jess watched her go a moment then forced his attention to the tidying up. Lorelai shouldn't be expected to do it all on her own. Last night had been fun, just as it always was when he spent an evening with the Gilmore girls. The only part that hadn't been good was seeing Rory bring that idiot Dean home. Jess wasn't sure when he had quite decided that the other guy was so stupid or awful, though he suspected it was in the split second when he first realised he might be trying to get into Rory's life.

"You're going to miss her being around, aren't you?" asked Lorelai as she and Jess tidied up together.

"What? Rory?" he checked, as if he didn't know.

"No, Queen Amidala of Naboo," Lorelai rolled her eyes. "Don't pull that James Dean crap with me, Mariano, I've known you way too long," she reminded him.

Immediately, Jess knew he should've known better than to ever even try it with Lorelai. She was way too smart, and she was right, she had known him too long.

"She's always been there," he shrugged, looking at the carpet. "And now, she'll be there less."

"But it won't change anything for you two, not really," she assured him, putting her hand to his shoulder until he looked up and met her eyes. "You mean the world to her, Jess, just like I know Rory means the world to you. You're just about the only person that gives me competition in the BFF stakes, so stop worrying," she told him. "Besides, if you just applied yourself a little, you're smart enough, you could be going to Chilton too."

Jess rolled his eyes at that.

"Not my deal, Lorelai, you know that," he said definitely, stacking up glasses and heading for the kitchen. "Rory's the academia nut. I'm just... That's not me," he shook his head. "I don't want it like she does, but I know she'll do great, just like always," he smiled fondly as his eyes drifted to Rory's bedroom door.

That look was not lost on Lorelai and it gave her a good feeling of warmth as well as a terrible moment of cold dread as she realised what it could mean in the future.

Right on cue, the door opened then and Rory stepped out in her full Chilton attire. She was a picture in her pressed shirt, dark blazer, and newly hemmed skirt that didn't quite make her knees.

"Wow, you look great!" said Lorelai happily.

It was only when Jess didn't say something similar that she cast her eyes sideways and saw the way he was staring. Oh damn, this was not good, Lorelai realised too late, and once again, Rory didn't notice at all.

"What do you think, Jess?" she asked, all innocence and wide eyes.

"You... You look great," he told her, clearing his throat twice just to get that many words out and running a hand back through his hair. "I gotta go help Uncle Luke," he muttered next, grabbing his jacket from the back of the chair and practically running for the back door.

Rory frowned as she walked over to her Mom, the pair of them watching Jess' hasty exit.

"What's wrong with him?" she asked Lorelai, who only sighed.

"One thing you gotta learn, Rory," she shrugged. "Sometimes, there's just no explaining boys."

_To Be Continued..._

**A/N2: If you're reading this and you have any opinions at all, a review would be awesome - thank you! :)**


	5. Chapter 4 - Routine Maintenance

**A/N: This chapter got loooong, but that's a good thing, right? Feedback is welcomed and adored - thank you ;)**

_**(For disclaimer, etc. - see Prologue)**_

Chapter 4 - Routine Maintenance

Rory had been attending Chilton for three weeks. From the perspective of her friends, it seemed like a whole lot longer, Lane was missing her only real girl-friend terribly. She loved Jess like a brother, she really did, but it wasn't the same. Taking to him about certain topics was entirely impossible. Talking to him about anything was tough lately as he seemed to snap at just about everything and today was no different.

Jess and Lane were sat opposite each other in the cafeteria, her picking at her food, him with his feet up on the table, reading a book and eating an apple. The most conversation she had got out of him so far was when they first walked in. She asked if he was having a good day, received a curt 'fine', and that was that.

"I miss Rory," Lane sighed heavily, dropping her fork down with a clank.

"Yeah?" checked Jess, looking at her over the top of Allen Ginsberg's 'Howl'.

"Don't act like you don't!" she snapped. "I know the reason you've been so grumpy lately is because she's not around, so don't even try to deny it."

Jess dropped his feet down off the table, pushed a marker into his book, and leaned forward towards Lane.

"I never said I didn't miss her," he admitted. "But if she doesn't have time for her friends anymore?" he shrugged. "Nothin' I can do about it."

Lane's eyes went wide at the accusation, more than wide when Jess started stealing fries off her plate, his apple long gone now. Rory hadn't abandoned them, she had just gone to a better school. She had to go, it was for her education and her future. Lane didn't begrudge her friend that and was sure that Jess couldn't either. Of course, Rory wasn't always at Chilton or even in Hartford. She was around Stars Hollow and yet Lane had seen very little of her. She wasn't sure if Jess had much contact with their mutual friend lately, but the way he was talking suggested not.

"I guess she's busy studying," she considered aloud. "She had to catch up on a lot of reading, at least that's what she said, and Rory doesn't lie."

"No, she doesn't lie," Jess agreed, thoughtfully chewing on another fry. "But she's got other priorities now. I'm starting to think maybe we aren't as high on her list as we thought."

"Maybe," said Lane grudgingly.

She didn't want to think that about Rory. From the age of eleven, they had been such good friends. Lane and Jess got along well, but they were both more friendly with Rory than with each other. She was the glue that held their little group together, and without her everything felt strange, unbalanced, and weird.

"Y'know, last week I saw Rory, and I was about to run across the street to talk to her when I saw her head into Doose's market," said Lane then. "She was in this really intense conversation with that new guy - Dean Forester? I waved through the window but she didn't see me, and then my Mom saw and kind of freaked out because I was within three feet of a boy," she sighed heavily.

Jess smirked a little.

"I can't wait for the day when dear old Mrs Kim realises how much you hang out with me," he grinned wickedly. "Pretty sure her head would spin around and explode."

"Not funny!" Lane smacked his hand as he went for another fry from her plate. "The day my Mom realises that my good friend Jess is you, and not a coincidentally named female friend, _that_ will be the day that I die!" she insisted.

Jess knew it was mean to tease her, but honestly, it was easier to focus on Lane's problems than his own. Rory liked Dean. Just that very thought made him want to kick the crap out of the nearest person that got in his way. Time that Rory could've spent with Lane, or better yet with Jess himself, and she had spent it in the market, talking to good old farmboy, Dean. It was enough to make a person crazy, which Jess tried not to let happen to him. Unfortunately, it was hard to ignore his general abandonment by Rory when Lane was reminding him of it.

"You think we should talk to Rory about the whole not being around thing?" she asked after a while.

Jess was so caught up in his own thoughts, he didn't respond immediately. He heard her, but it sort of hadn't occurred to him for a moment that he needed to answer. Eventually he shook his head.

"I don't know," he admitted. "She'd have to actually be around for us to talk to before we could bring up a topic."

It shouldn't hurt like this, that was what Jess told himself, even as Lane started to ramble on about how she was uncomfortable with accusing Rory of any wrong-doing. Jess didn't want to be jealous of a school, and especially not of another guy. He was Rory's best friend, if she had spare time she would spend it with him, so clearly she was just busy. He kept trying to tell himself that, to give her the benefit of the doubt, because hell, if she hadn't done that enough times for him over the years.

Still, the facts couldn't be twisted to his satisfaction, not quite. The school hours and the travelling, that Jess could forgive. Even the extra time Rory needed to spend studying. What he couldn't help was feeling sick about the time she spent with Lurch or running back to Hartford to la-di-da with her fancy grandparents. As if all this weren't bad enough, his attention was suddenly taken by a bunch of idiotic jocks all laughing over some joke they thought was so great. At the centre of them was Dean.

"You think if I punched him in the face it'd have any effect on his pea-sized brain?" he asked, not really to Lane so much as in general.

"Who? Dean?" she asked, a little confused since she had been talking on a completely different topic.

"Let's find out," he muttered as he moved to get out of his seat. "Lane!" he complained when her hand clamped onto his shirt and pulled him back. "God, what is your childhood trauma?" he asked, sure that one false move would have ripped a gaping hole in his favourite blue shirt.

"You are not going to punch, Dean," she said firmly, not at all phased when he glared at her. "Seriously, Jess. Rory would go crazy, and you'll just get into trouble again."

He knew she was right. It wouldn't be the first time he was in trouble for fighting. Usually between Rory and Lane they would calm him down whenever he started to feel like he wanted to lash out. Often it was when somebody made dumb comments about him hanging out with two nerdy girls or because his parents weren't around. Occasionally, it was because somebody started in on Rory or Lane themselves - Jess would not let that stand. Still, when they begged him not to make a fuss, he usually backed down, for their sake more than his own. If he went and socked Dean now, he would definitely be in trouble, and what excuse would he really have? He hit the guy for fun? Because he dared to like Rory? It was lame and Jess knew it.

"I gotta get some air," he muttered, turning away from Lane and stalking out of the door.

Left completely alone at her table, Lane looked around at the rest of the room and sighed. A moment later she was hurrying out to find someone to talk to, or better yet somewhere to hide. Everything was definitely wrong since Rory went to Chilton, and Jess was more out of whack than anyone since she'd been gone.

* * *

It was almost a complete fluke when Jess was walking through town and spotted Rory on the way back to her house. He figured she had to be around somewhere, but she so rarely checked in with him, he wasn't entirely shocked to realise she was probably avoiding him. After the day he had, his conversation with Lane, the way Dean had wound him up, however inadvertantly, it was too much. It was time Jess and Rory had a little talk about friendship and what it was supposed to mean. He barely checked for traffic as he strode across and down the street to the Gilmore house.

"Hey, Jess!" Babette called as he passed by her porch. "You ain't seen my baby Cinnamon around, have you, sugar?" she checked. "I can't think where that cat's got to..."

"Not lately," he told her, hardly stopping moving for a second. "You try under the porch? That's where he was last time I found him," he reminded her.

"You, you're an angel!" she exclaimed happily, but Jess spared her only the smallest of smiles before he continued on to Rory's front door.

He was too mad right now to be dealing with Babette and her cats. He had to have things out with Rory and it had to be now before he changed his mind, made some lame excuse to himself and chickened out. The fact was, the two of them were so close and very rarely fought. It had to be something damn important to knock their friendship even for a day, an hour. Today just had to be one of those days, unfortunately.

Jess knocked on the front door with a force to be reckoned with. For a minute he thought Rory was going to ignore him entirely, but just as he was about to try again, she opened the door.

"Jess, I..." she began, but he didn't have time for excuses.

"We need to talk," he said definitely, pushing past her before she could protest.

"Jess, now isn't a good time," she complained. "I have studying and homework."

"Yeah, you sure have a lot of that lately," he countered, facing her across the entrance hall with his arms folded across his chest. "Funny, 'cause I figure even people who go to Chilton get free time now and then."

"Of course," Rory frowned. "And when I get free time, I'll spend it with you."

"Really?" he checked. "Y'know I thought that was how it would be, but then I'm talking to Lane, and it turns out, neither of us can remember the last time we saw you for more than ten seconds at a time," he told her, volume rising without him really noticing as he got more and more mad. "Oh, well, there was that one time," he snapped his fingers and pointed an index finger at her, as if the idea just came to him. "Didn't Lane see you through the window of Doose's market a couple of days ago? That's right, you were the one making cow eyes at the new bag boy," he sneered.

"I don't make cow eyes!" Rory snapped, copying his stance with arms folded, a little defiant but mostly defensive. "And what? It's a crime for me to go to the store and talk to a person now?"

"No, it's not a crime," Jess rolled his eyes. "But that wasn't a person, it was Dean Forester. Besides, Lane and me, we're supposed to be your best friends, and we've hardly seen you for weeks now!" he continued to rant, knowing this was way more about himself than it ever was about Lane, but that wasn't the issue in this moment. "Kinda thought when you finally came up for air from all your books and fancy uniform, you might actually have time for us!"

"I do!" Rory tried to argue, but he just wouldn't let her talk - Jess was on a roll.

"See, the words are great, Rory, but where's the proof?" he demanded. "You say things won't change, that you'll still be around, but where are you? Off with your fancy Chilton friends, is that it? Are we not good enough anymore? C'mon, Rory, explain it to me! I know I'm not all educated and fancy like your new friends, but I understand plain English!"

"I'm sorry!" she yelled then, loud and sudden enough to make Jess actually back up a step.

Still, her sudden outburst wasn't what really shocked him. It was the tears running down Rory's face that blew his mind. Rory didn't cry. Well, that was a lie because of course she did cry sometimes, at really sad movies, or when something genuinely devastating happened, but she wasn't one of those girls that crumbled at the littlest thing. Any fight she and Jess had ever had, and there had been a few, she got mad but she didn't cry. This wasn't just a few tears either. As he stood there and watched, Rory's hand went to her face and great heaving sobs started to shake her body. Jess felt sick.

"Rory?" he said, taking a careful step forward. "Rory, I didn't mean..."

She fell into his arms as soon as he was close enough and Jess hugged her close on instinct. Something was not right here. Yes, he came to bawl her out about not being around, and he knew that might cause a negative reaction. He expected her to either be apologetic and such, or to argue with him and get mad. He hadn't been ready for this. As upset as she seemed to be, Jess wasn't so sure he could've caused this all by himself. He certainly hoped all this wasn't about him, but then that meant he needed to figure out what was actually wrong and help his friend figure out a solution.

"Talk to me, Rory," he urged her when her crying quietened down some. "Look, I'm sorry, okay? I didn't mean to... to yell so much, I just..."

"No, I'm sorry," she sniffled, lifting her head up off his shoulder, meeting his gaze with her red-rimmed eyes. "I haven't been around, not for you, or for Lane, and I hate that," she admitted. "I hate that Chilton is making me a bad friend!"

"You're not a bad friend," Jess back-tracked on everything he just said at the sight of her genuine tears, and the look on Rory's face proved she could hardly believe it. "Yeah, okay, you've been pretty absent, but somethin' bigger is going on here, right?"

Jess knew he was right. All the tears and crazy apologies, this wasn't Rory. There was something she hadn't told him, maybe hadn't told anyone. There was even a chance that her seemingly avoiding him, and even Lane, had been because she didn't want to have to share some awful secret. All kinds of scenarios started running through Jess' head, most of which made him want to throw up.

"C'mon, Gilmore," he teased her, wiping a stray tear off her cheek and forcing a smile. "Tell me who I need to punch to make it better, and I'm there. Tell me it's Forester and I'll do back flips on the way," he smirked.

Rory rolled her eyes and smiled because she couldn't help it. It wasn't funny. She really didn't want Jess to hit Dean, or anybody for that matter. It was sweet how he wanted to help her though, just like always, even when he had been so mad at her before. Her Mom always said that crying was a great tool to be used by all women, whether it was to get out of a parking ticket or divert attention from the fact they hadn't made good on a promise to a friend. Rory wouldn't ever use such a trick on Jess, that wasn't what this was. He was right, there was a problem, but it was nothing her friend could fix with his fists. Taking a deep breath, Rory pushed her hair back behind her ears with both hands and then headed to her bedroom. Jess followed because he didn't know what else he was supposed to do. He watched as Rory reached under her mattress and produced an essay in her own handwriting which she duly hand to him. There at the top in a big red circle was the problem - Rory's first ever D grade.

"Wow," he said in genuine surprise. "You got a D? Rory Gilmore got a D?" he checked twice, because honestly, he figured there just had to be some mistake.

"I've been studying _so_ hard," she insisted. "I read everything, _twice_. I made all the notes, and I tried, I really did, and this is what I get? A D? I've never gotten a D, Jess, not ever."

"I know," he agreed, nodding absently as he started to read her essay from part way down.

It looked okay to him, but then he wasn't an English professor at a private school. The curve was higher, a lot of brains all in one place together, it meant the bar was raised. Rory could hit the top even at Chilton, Jess was certain of it, but she had started after everybody else in her grade and she just wasn't used to the pace. This he started to tell her, as she flopped down to sit on the edge of her bed, looking sad as ever.

"I have to do better!" she insisted. "Somehow, I just, I have to."

"And you will," he promised, sitting down beside her and tossing the essay to one side. "It's one assignment, Rory. One lousy essay, and next time you'll do better, and before you know it you'll be back up to that A you're used to. You just gotta have a little faith in yourself," he told her, nudging her shoulder.

"I wish it was that simple," she sighed, leaning into him. "Sometimes I wish I just stayed at Stars Hollow High. I had you and Lane, I knew what I was doing, and everything was easier..."

"And where's easy gonna get you?" he asked, cutting in without a care. "That mess on your wall that says you're destined for Harvard? You can't get there with a diploma from Stars Hollow, Ror. It's gotta be Chilton. You were made for that place, you're too smart to be anywhere else."

"You're still at Stars Hollow, and you're just as smart as me," she argued, perhaps the lamest come-back she could've used.

"Different kind of smart, maybe," he admitted, smiling at her gall. "You know I don't care about this junk, not the way your school would want me to. I don't have big college plans, the whole career thing. It's not me, but it is you," he reminded her. "For what it's worth, _I_ know you can do this, even if you can't believe it right now."

Rory loved how much faith he had in her. Jess really was a good friend, always had been, and she wondered how she would ever do without him. When the day came that she really did go off to college, and Jess left town for his world-wide wild adventures that he talked about so often, she wondered how their friendship would fare. She hoped rather than believed it could hold firm when miles and even oceans stood between them.

"I have a test in three days," she said eventually, sniffing one more time. "I have to ace it if I want to get my grade up, but it's all this Shakespeare stuff, it's just so much to learn," she admitted, putting a hand to her head as if the very thought of all the studying still to do literally caused her brain to ache.

"Hey, it's cool," Jess insisted, reaching for the complete works of Shakespeare sat on the desk. "You need to learn it, I'll help you. We'll do it together," he promised.

Rory smiled a watery smile.

"You would do that for me? After the whole yelling at me thing?" she said, gesturing back towards the hallway where said yelling had taken place. "You were so mad..."

"I wasn't _so_ mad," he rolled his eyes. "Anyway, I didn't know you had all this going on. I'm a jerk, whatever."

"You're not a jerk," she insisted, frowning at the fact he would ever say such a thing about himself. "You're the best friend I ever had! Plus you get bonus points if you can help me ace this test at the end of the week."

Jess smiled at that as they both took a seat at the kitchen table, him still flipping through her textbook. He had read the whole works of Shakespeare before, but how much he really remembered remained to be seen. He would do his best though, just like Lorelai would, even though Rory's Mom wasn't so much book-smart as she was all the other kinds of intelligent.

"So, how come your Mom isn't helping with the studying?" he checked, glancing up to see Rory putting on the coffee pot.

"Because she doesn't know," she admitted without looking at him. "I couldn't tell her about the D, I just, I couldn't," she squirmed.

"Oh, c'mon!" Jess got her attention. "Lorelai is not the type to go postal over one lousy D, Ror, you know that."

"It's not that," she shook her head. "I just don't want her to know right now, okay? She has enough going on with the inn. She already does so much for me, finding the money to send me to Chilton and all. Please don't tell her, Jess."

He didn't like it. Lying to Lorelai wasn't cool, and keeping things from her was still lying, albeit by omission. Still, this was Rory asking. He had no choice.

"Okay," he nodded once. "Now, let's put the hurt on Shakespeare," he said, pointing his index finger into her text book.

This so wasn't what he came here for today, but Jess had to notice that at least he was now getting to spend time with Rory, even if it did mean studying to do so. That was fine by him, just because it was her.

_To Be Continued..._


	6. Chapter 5 - Don't You Make

**A/N: The more I get into GG and Literati, the more I wish this fandom wasn't practically over before I got here *sigh* If you're reading this, please be a star and let me know with a quick review! Thanks to those that are already doing so :)**

_**(For disclaimer, etc. - see Prologue)**_

Chapter 5 - Don't You Make My Green Eyed Monster Blue

"Ugh, this is impossible!" Rory groaned when she got the answer wrong to a third question in a row. "It's so stupid, I'm never gonna get it, and I'm gonna fail, and drop out of Chilton, and... and wander the streets as a hobo!"

Jess held back a smirk but failed at keeping his eyeballs in check as they rolled quite obviously. Rory could be such a drama queen. She got that from Lorelai, he knew, and he could handle it. Of course, laughing at her sometimes worked, but right now that seemed like the worst possible plan. Instead, he got up and stepped into her path as she tried to pace by him one more time.

"Rory, breathe," he told her, grabbing her wrists in his hands. "You're burning yourself out, that's why this junk isn't sticking anymore," he told her.

Jess knew how freaked she was, mostly because she didn't call him on his use of the word 'junk' for the English Lit she was learning. Him and Rory, they were just about as smart as each other, the difference was this was all so important to her. For Jess, High School was something he had to get through so that he could actually go ahead and live his life. He had no dreams of fancy colleges and big time careers. He would however do anything Rory needed to get her there, because he knew how much it meant to her.

"I can't stop, Jess," she said, shaking her head. "If I stop now what's already in there will fall out and..."

"If it falls out I'll stuff it back in!" he said with determination, immediately wondering at this analogy they had going when she looked at him oddly. "Rory, c'mon. I know you can get by on your fair share of junk food and coffee, but you gotta at least take a break, even if you're not gonna eat anything that's actually in a food group."

"Yes, Dad," she smirked, a look she most definitely learnt from Jess himself.

"Hey!" he balked at the sarcastic term. "Don't start with me. Be glad I'm still here helping out. Y'know you're making me be the rational one in this partnership. That's not a good look for me."

Jess hated being the sensible one, that was always Rory's job, and they both knew it. When the sluttiest girl in town asked him out last year, his best friend advised him not to go there. When some of the 'cool' guys in school got him smoking a few months back, it was her that bought him the nicotine patches and hid his cigarettes. It wasn't as if he never helped her out with anything ever, but Rory was the girl scout, and Jess was most definitely the hoodlum, even if he was much less bad than he might've been without the influences of Luke, Lorelai, Rory, and Stars Hollow as a whole.

"I'm sorry," said Rory with a sigh. "I'm being all crazy over this test, I know I am, but it really, _really_ matters to me, Jess."

"I know that," he nodded once. "But if I'm helping you here, you gotta listen to me. It's not all about cramming until your head explodes. Take a break, take a walk," he advised her. "You need to."

"I do need to," she agreed. "I swear I don't know what I'd do without you sometimes," she smiled then, reaching out to hug him.

"Yeah? Be glad you're not ever gonna have to find out," he told her softly as he hugged back a moment. "Now, go out, walk, breathe deep," he urged her, practically shoving her towards the door.

"You're not coming with?" asked Rory as she pulled on her jacket - Jess shook his head.

"If we go together, you're gonna keep talking about Shakespeare," he told her, knowing it was true. "You walk alone, you think about something else. I'll go check in with Luke, pick us up a decent lunch, meet you back here in a half hour, okay?"

"Okay," she smiled and nodded, and then headed out the back door.

Jess let out a long breath. He had a headache, and it was really pounding. It wasn't Shakespeare's fault, but he was getting really, _really_ sick of the guys work right now. This was why he hated school. The way you just had to go over and over things until it drove you crazy. If Jess wanted to read a book more than once, then he would. Being told he had to do so, to study the text, learn every fact, pick the whole thing to pieces, that was what made him crazy. He did this for Rory, because in his mind there was no choice but to do so. That didn't mean it made him feel any better about it.

Dashing upstairs, Jess raided the bathroom cabinet for a couple of aspirin that he dry-swallowed, then used the facilities before rushing back down to the living room. He grabbed his jacket from the couch and pulled it on before heading out the front door and off to the diner.

Uncle Luke would certainly take his nephew's mind off English Lit with his nagging and such. Jess didn't mind all that much. He knew he was a pain in Luke's ass sometimes, not always deliberately, but still. It had to tough on the guy to suddenly be handed an eleven year old and be expected to raise him. Of course, Jess had to think he got the worse end of the deal, his mother deciding to dump him and hardly ever call. No kid deserved that, Jess was pretty sure he hadn't, though honestly, he tried not to think about it much.

"Hey, Jess!" Luke called the second his nephew walked into the diner. "Jump behind here, would you? I'm lacking help today."

"No can do, Uncle Luke," he told him, with mock regret. "I'm still helping Rory study for the big test."

"What? You shrunk her down and have her in your pocket right now? Because I don't see her" Luke snapped back at him, rushing to serve another order to some cranky looking customers.

"Yeah, I turned my shrink ray on Rory. She's right here in my hand, you really can't see her?" asked Jess, holding out his open and decidedly empty right hand. "Say hello to Uncle Luke, little Rory," he smirked.

"Very funny. Hilarious in fact," said Luke crossly. "I can't understand why you're not on a stage with material like that. I gotta call Lorne Michaels and get you a gig."

"Did you just use the word gig in a sentence?" checked Jess, as he sat down on the nearest stool, not at all surprised when Luke breezed right by him with more plates and a scowl, refusing to rise to the bait.

"If you're not helping why are you here?" he asked on the way back.

"Rory needs real food, and I needed fresh air before my head explodes," sighed Jess. "Can I get two burgers and fries to go?"

"Real food?" Luke echoed, one eyebrow raised. "Burgers and fries aren't exactly a food group."

"Hey, we've been living on gummie bears, coffee, and microwave popcorn for the last God knows how many hours. Your burgers and fries are gonna be gourmet after that."

"Point taken," replied Luke, making a face at the very idea of eating such crap, especially first thing in the morning. "Two burgers and fries coming up. Caesar!"

Jess winced at the yelling as Luke walked into the back. His fingers ran over his forehead as he tried to force the headache away. The aspirin should kick in soon, he hoped. He would never learn to cope with the combined caffeine hit and sugar rush like a Gilmore could, not even after five years of practise. Checking his watch, Jess saw he had already been gone from the house ten minutes. He wanted to get back before Rory did, so there wouldn't time to hang around once Uncle Luke brought out the food. He figured they could get Rory all sorted on the rest of Shakespeare's plays this afternoon, take another break, and blast the sonnets in the evening. She was bound to ace this test tomorrow, there just wasn't a second option. In the meantime, Jess needed rid of this headache. He let his head fall forward onto the cool hard surface of the counter until he heard the rustle of a paper bag and smelt greasy food near his nose.

"You okay?" asked Luke with a frown that Jess didn't see until he picked his head up and looked.

"Fine," he said shortly. "Just not sure who's gettin' more burnt out from the studying, me or Rory," he rolled his eyes.

"You're a good friend," his uncle told him with a smile. "I'd say she doesn't deserve you, but it's Rory, so..."

"Yeah," Jess nodded once in agreement and reached for his back pocket.

"Hey, these are on me," Luke waved away his offer of payment. "Get back to those books, help our girl do us proud."

Jess smiled, muttered an awkward thanks and swiftly left. He moved quickly across the main street and down towards the Gilmore house. He was a couple of blocks away when he realised Rory was up ahead... and she wasn't alone.

"Tall, dark, and forehead," he muttered as he took in the sight of his best friend giggling like a giddy schoolgirl at something the farmboy had said.

Jess felt his hands curl into fists. Man, he hated that Dean Forester. He had no real concrete reasons for said hate, it just seemed like an instictual reaction that Jess had no control over. Sure, he could come up with a few decent excuses for his inner rage, but he didn't like any of them so he pushed them all aside as dumb and pointless. All he really thought about was how much fun it would be to kick this guy's ass to the moon.

Walking a little closer, Jess actually heard the grating sound of Rory's fake laugh. It had to be fake, he never heard her laugh that way in the whole five years they'd been friends, and he hated it! He hated that maybe she had this special laugh especially reserved for Loser Lurch. Hated it so much he wanted to throw up!

There was a moment when Jess thought about storming over there, laying down the law about studying being more important than whatever Rory was discussing with Dean. He could say the food was getting cold or something equally as lame, but any excuse would be just that - lame. He still had no good reason to punch this guy out, and Jess really didn't think he needed one, except for when it was done and everybody asked why. Anything he said in response to that would sound stupid or... No, he wasn't going down that road. Turning away, he took a different route back to the Gilmore house, throwing the bag of food from Luke's diner down on the kitchen table as soon as he got inside. His hands gripped the back of a chair so hard his knuckles turned white. A second later, Jess picked up an empty soda can and threw it hard across the room where it hit the wall with a crack. Lorelai immediately came rushing down the stairs.

"What the hell...? Jess?!" she yelled as she came across him already picking up the fallen can. "What were you trying to do? Scare me to death?"

"I didn't know you were here," he grumbled something that might've been an apology, but Lorelai couldn't be sure.

"Geez, what is the matter with you? I come home to change after a frighteningly epic spill disaster at the inn, there's nobody here, and suddenly it sounds like the Battle of Gettysburg in my kitchen" she explained, exaggerating the way only a Gilmore could. "What's going on? Where's Rory?"

Jess bit his lip and turned away. He couldn't talk to Lorelai about this, he just couldn't. There was no way in hell he was going to explain how much he wanted to smack Dean in the mouth. That would throw up all kinds of questions, because Lorelai always, _always_ had questions, and Jess just wasn't in the mood to get into that right now. He doubted he ever would be.

"We were studying," he said eventually, still with his back to Lorelai until he was sure he could talk without accidentally biting her head off. "I'm helping Rory wrap her brain around all this Shakespeare stuff so she can ace her test tomorrow," he explained, turning to face his best friend's Mom.

"Oh, okay" Lorelai nodded. "Well, that's really great of you, Jess. I'm just a little confused," she said, rubbing her forehead as if it ached. "I mean, Rory mentioned a test, briefly. Nothing about it being so important, or about needing study help. I know I've been busy lately, but I'm always here if she needs me, she knows that. I thought she knew that..."

"She does," Jess cut in on the rambling that was bound to go on indefinitely if he didn't. "It's just..." he began, stopping short of the confession when he met Lorelai's worried eyes.

This wasn't fair. He promised Rory he wouldn't tell her Mom about the essay that only earnt a D grade, the reason she had to ace this test just to bring up her average in English Lit. Jess knew if he did this he would wind up regretting it, but as he tried to convince himself what a bad idea it was, he heard that stupid girly laugh that Rory only used near Dean and his blood boiled in his veins for no reason he was willing to think about.

"She got a D," he blurted out, and then it was too late to take it back.

"I'm sorry, what?" asked Lorelai, shaking her head, literally knocking her palm against one ear as if she needed to unblock something from it. "A D? As in the grade below A, B, and C?" she checked.

"That's usually where it sits," Jess shrugged.

"No, no, no, no," Lorelai almost laughed then, though it sounded closer to hysteria than true amusement - Jess wasn't surprised. "Rory doesn't get Ds. My Rory, _our_ Rory," she emphasised, pointing a finger into her own chest and then waving the same digit between herself and Jess emphatically. "Rory does not get D grades. Never."

"Well, she did" he confirmed. "Her English Lit paper was... it was worth a D apparently. Now she has to knock this test out of the park if she want to drag herself back up to a decent passing grade, hence the help."

When he finished speaking, Jess found his voice was a lot quieter than when he had begun. He refused to think that it was really guilt that was causing his voice to falter, though he suspected that was exactly what it was. He knew for sure when Rory appeared at the back door with a look of panic on her face. What the hell had he just done?

"Oh, no. This isn't right. This will not stand," Lorelai was insisting as she grabbed up her coat and purse. "Rory, we're going to fix this. Mommy's gonna go have a little talk with Mr, er... Mr Medium? Mr Mediator?"

"Medina," Jess supplied, when all Rory seemed capable of was opening and closing her mouth like a landed fish.

"Medina, right, got it," the older Gilmore snapped her fingers and pointed, then she was rushing for the door and there was just no stopping her.

"Mom!" Rory called after her, giving chase.

Jess let them both run by and didn't move at all. Rory expected when she came rushing back again a few moments later to find him still there, but strangely he was gone, the back door swinging on its hinges in his wake.

_To Be Continued..._


	7. Chapter 6 - Two for a Pair

**A/N: Time for our boys to truly realise what our Gilmore girls mean to them! Thanks to those who leave reviews - you're the best! :)**

_**(For disclaimer, etc. - see prologue)**_

Chapter 6 - Two for a Pair

"_You_? You got asked out on a date?"

It was just a little offensive to Lorelai that Luke looked so shocked when he asked that question. Maybe she would be all the more put-out if she didn't understand that Luke just wasn't all that subtle sometimes. Plus, in all the years they had known each other, and that was a good five or more at this point, she hadn't really dated all that much.

"Is it so hard to believe?" she asked, appearing a little more affronted by his tone and his question than she actually was - it was fun to make Luke squirm sometimes.

"No! No," he immediately shook his head. "I didn't mean that exactly, I just... Who's the lucky guy?" he settled on eventually, knowing any excuses he made were just going to make matters worse anyway.

Lorelai's smile grew as she imparted her news in hushed tones across the counter.

"His name is Max Medina," she grinned. "I met him at Chilton."

"So, he has a kid there?" Luke guessed, as he grabbed her cup and started to refill it with the strongest coffee in the diner.

"Well, he knows kids that are there..." replied Lorelai, finding it was her turn to squirm when she felt Luke's eyes on her in a gaze of confusion. "He's an English teacher."

"Rory's English teacher?"

"Sssh!"

It wasn't fair to judge her, and Luke knew it. Lorelai might come off kind of crazy at times but she was one smart cookie. If she thought it was okay for her to be going on dates with this Max guy, then he wouldn't argue with that. What Luke couldn't explain was the knot that had formed in his stomach the moment Lorelai mentioned dating anybody at all. It wasn't as if they were ever romantically entangled themselves. From the day they met, they seemed to have been destined to become the best of friends, as had Rory and Jess. Nothing ever happened, no dates requested, no moves made. It wasn't as if the thought hadn't crossed Luke's mind, but he didn't exactly have the best history with women. One too many heart-breakers left him feeling cautious, especially since he had a kid in his life to consider these days. Lorelai did too, and Luke wouldn't see Rory or Jess hurt for the world.

It was only when Lorelai started waving her hand in front of his face that Luke realised how long he must've been lost in deep thought. He shook his head and refocused his eyes on her.

"Sorry, what?"

"I said, do you think I'm crazy?" Lorelai repeated, then off Luke's look she clarified. "For actually considering saying yes when Max asked me out? I mean, I might say no... I should probably say no, but there's a good chance I'm gonna say yes, so... Crazy?"

"What's it got to do with me?" Luke shrugged, trying to busy himself with orders for customers and not look directly at her. "I'm not your father, or Rory's father. I play no part in your dating life."

Perhaps his tone was a little harsh when he considered it a moment later, but this was maybe the most awkward conversation Luke had ever had in his life. Well, possibly the second most awkward after the one he had with Jess a while back about the birds and the bees. Just one brief thought of that talk made Luke shudder even now, but this with Lorelai was a very close second.

They never had that relationship, not ever. There wasn't so much as a drunken fumble or a desperate pass in the last five years and more. Luke didn't really want things to change, not one way or the other, and yet knowing Lorelai was going on a date, a real one that could actually lead to something real, it made him feel sick. A subject change was most certainly in order, and thankfully he had a topic in mind that he needed to raise anyway.

"Listen, I actually have a favour to ask you," he said with a smile that he hoped came off okay.

Lorelai was rarely easily wounded by words said to her. Given all the things she had been through, Luke highly doubted that his snippy tone before would really bother her. If it had he would apologise, but already she was smiling again. The woman bounced back faster than a rubber ball, and that was just one of many things to love about her. It still didn't make him feel good about snapping at her but if she was letting it go, maybe it hadn't seemed so bad from her side of the counter...

"Sure, whatever you need," she told him easily as she sipped her coffee - that just made Luke feel more awkward.

"Look, I'm sorry if I was... y'know, if I snapped about the dating a teacher thing," he said in a low voice that no-one else in the diner should hear. "I'm not judging, really."

"I know, it's okay," Lorelai nodded then. "Honestly, I know how it sounds. To think I went there to yell at the guy for giving Rory a crappy grade," she rolled her eyes. "Well, crappy isn't fair, it's only... Okay, you can't talk to anyone about this," she whispered, moving in closer. "Rory got a D, and apparently it's genuinely all her paper was worth."

"Ah, does this explain why she and Jess have been cramming Shakespeare like crazy people?" Luke checked. "To get the English grade up for Rory?"

"Bingo!" Lorelai nodded once, pointing at Luke with her index finger. "Got it in one."

"Uh-huh," his head bobbed in understanding as he moved away to serve another customer.

Lorelai watched him move away and then come back. He was about to walk right by, she could tell, but her fingers grabbing his sleeve stopped him.

"Hold on a sec, you mentioned a favour you need but you didn't say what," she reminded him.

"Oh, yeah!" Luke almost literally face-palmed as he realised his mistake. "It's actually about Jess. See, I have to go out of town next weekend. An old friend of mine called me up, he's having some problems. Long and the short of it, I said I'd go help him move apartments and... well, I trust Jess, I do, it's just, he's still a kid, even if he's determined to tell everybody he's all grown up..."

"You don't want him to stay in the apartment alone for the whole weekend," said Lorelai with a knowing look and an understanding smile that she wore so well. "Luke, you know he's always welcome at our place. Our casa is his casa, Saturday, Sunday, and the night in between," she agreed easily.

"That's great, thank you, Lorelai," said Luke with genuine appreciation. "Er, but could you maybe let him stay Friday night too?" he asked awkwardly. "I kinda wanted to head out before the roads get filled up with weekend traffic..."

"Oh, Friday is..." Lorelai faltered a moment but then stopped and smiled widely. "Um, yeah, Friday will work, no problem"

Luke had to move away almost immediately as more customers came into the diner. Kirk was asking a hundred questions about the menu and Taylor was already complaining about the diner being over-capacity if a few people didn't leave soon - fire violations were mentioned and Lorelai was pretty sure it was going to get ugly before long. It was tough for her to concentrate though, her mind already spinning over Luke's request. Having Jess over at the Gilmore house was never a problem, except Friday night could be very awkward. There was no way she could swerve dinner at her parents' house. She and Rory both had to attend, that was the deal. If she tried to wriggle out that would cause issues. It might even prompt her mother to accidentally on purpose reveal to Rory why the Friday night dinners were necessary. Lorelai wasn't ready for that yet. The only solution she could come up with that didn't make her a complete bitch in at least one person's eyes was to take Jess to dinner... with Richard and Emily.

Lorelai felt sick at the very thought of subjecting poor Jess to her parents, and of allowing said parents to find out anything more about Rory's life than they needed to know. Unfortunately, it seemed the lesser of all the evils. Taking back a favour she had already agreed to with Luke, or leaving Jess home alone, Lorelai didn't like the idea of either of those things and knew Rory wouldn't appreciate it either. Nope, it seemed the only avenue left open was calling Emily and asking if there was room for one more at her table just this once. Lorelai reached for her cell phone, stared at it a moment, bit her lip, and then put the thing away again. Later. She'd call later.

* * *

"C'mon, Ror. You can't stay mad at me forever," said Jess, tapping on her window one more time.

He knew she was in there. It was too early for her to have gone out and the fact the key was missing from under the turtle by the front door proved something was up. Lorelai was at the diner alone, and it wasn't a school day, so Rory was likely to still be holed up in her room. Besides, Jess had seen movement of shadows from beyond the window pane that proved it, even as his friend tried to stay out of view.

This was getting pretty boring now. He had been here a half hour, knocking on the glass, trying to encourage Rory to just let him in already so they could talk. Maybe Jess should say he was sorry for what happened, but honestly, he'd rather do that face to face, not around corners where he couldn't even see the person he was talking to.

"Okay, fine, have it your way!" he said at last.

Rory was smart in her books and her school work, and yet not quite bright enough to realise that Jess was not going to give up here. After knowing him so long it ought to have occurred to her that bolting the front and back doors was nothing against his kind of perseverance. She realised her mistake when there was a clatter on her desk and a couple of trinkets went tumbling onto the carpet as Jess came through her now open window one leg after the other.

"Jess! What are you doing?" she asked crossly, getting up off her bed to stomp over to him.

"Riding a unicycle, can't you tell?" he said, every word dripping with sarcasm, as usual.

Despite being so very mad at him, apparently, Rory grabbed his arm and assisted in his inelegant arrival in her room. The moment he was on his feet, she shoved the window closed and set her desk back as it was before his intrusion.

"Take a hint, Jess," she snapped, even as she fussed over her things. "When somebody locks the doors and doesn't answer when you knock, it means go away."

"Really? That's what that means?" he rolled his eyes at her explanation, grabbing Rory's wrist when she tried to storm by him a second later. "Will you just stop and listen to me for a second?"

"No. I don't want to hear it!" she told him crossly, pulling her hand free and folding her arms across her chest defensively. "You promised me, Jess. You promised you would not tell my Mom about my grade and then you want ahead and did it!" she told him angrily.

"Hey, I didn't promise!" he protested. "I never promise, it's not worth the hassle when things get screwed up and I have to break it."

Rory huffed and turned her back on him. She did know that was true. Jess had issues with literally promising things, she guessed because so many promises had been broken to him, especially where his Mom was concerned. Still, Rory always took him at his word and believed him when he told her something. He said he wouldn't tell and he had. Okay, it did sound a little childish, and actually everything had worked out fine, but that wasn't the point. He still betrayed her trust.

"Rory, come on," he urged her, putting a hand to her shoulder, but she shrugged it off.

"You're my best friend, Jess!" she told him, though she refused to turn around still. "I thought that when we agreed on something... I thought I could trust you, with anything."

"You can," he promised in all but the word, his own anger dying down to nothing when he realised how genuinely upset she was about this.

Mostly Jess knew he was only ever mad at himself. Rory was right, he never should've told Lorelai about the D grade. No doubt she was going to do it herself after she aced her test, a high to counter the low when she had to tell her Mom that she failed at anything. Jess had spoilt that for her, and after he said he wouldn't. That wasn't right, and it deserved an apology.

"I'm sorry for the way things played out," he told her then, shoving his hands in his pockets since they had no other place to be. "It was just... it was one of those dumb situations, and Lorelai was asking why this test meant so much..." he shrugged pointlessly. "I know I shouldn't've told her."

"No, you shouldn't," Rory agreed, but the sigh as she turned around seemed to prove she wasn't going to hold a grudge anyway, thank goodness. "But I know you didn't mean any harm by it," she admitted then.

Jess didn't say a word. The truth was, a part of him did mean to cause trouble. Seeing Rory with Dean had turned on some raging anger inside his head, and the screaming voice wouldn't let up until he felt he got even for some betrayal he could never explain. Telling Lorelai about the D grade was revenge, in some small and stupid way, but what it was revenge for, Jess refused to think about that.

"Actually, I guess I should thank you," Rory half-smiled. "All that cramming you helped with? It did some good. I aced the test. Almost a perfect score," she grinned suddenly, so proud of herself as she had every right to be.

"Told you you could do it," Jess reminded her with a smirk he couldn't help, and yet was serious again in a second. "I am sorry about telling Lorelai..."

"Forget it," Rory shrugged then, her arms falling loose at her sides. "Honestly? Being mad at you is just hard work. Besides, I need someone to help me celebrate pulling my GPA back up to stellar levels," she told him. "You helped with the lifting, you get to help with the festivities. Plus, I have to share the freakiest news of the week with someone - my Mom got asked out by my Lit teacher! Which had no effect on my test, I hasten to add..."

Jess smiled, following behind his best friend as she headed for the kitchen. He doubted they'd find anything there that could be called real food, but it was where the take out menus lived, so that was cool. He was only glad to be in Rory's good books again and hear her rattle on about Lorelai and the apparently irresistible lure of the great Mr Medina.

Rory said it was hard work to stay mad at Jess, and that was something he couldn't feel bad about. Above all things, he hated when the two of them fought. He knew he could never be happy if she was unhappy. That was one more fact Jess refused to look at too closely for fear of what it really meant.

_To Be Continued..._


	8. Chapter 7 - Guess Who's Coming To Dinner

**A/N: I'm getting so many hits on this story, I've got 30 people following it, so may I ask that if you're reading you drop me a review and let me know? I don't like to sound like I'm begging, and I don't do threats about not updating until I get x number of reviews, I'd just really like to know you're there and what you like best about the story, etc. That'd be great. Thanks all :)**

_**(For disclaimer, etc. - see prologue)**_

Chapter 7 - Guess Who's Coming to Dinner?

It had taken almost the whole entire week for Lorelai to rustle up the courage for this phone call. It had been Saturday when Luke asked if Jess could stay at the Gilmore House over the next weekend, and she had easily said yes. The arrangements were as easy as they ever had been when Jess needed to crash on the couch and eat meals with his two favourite females. All that remained was for Lorelai to call her mother and check it was okay to bring young Mr Mariano over for the infamous Friday night dinner at the Gilmore mansion. Maybe she should've done this before Thursday afternoon rolled around. Honestly, there was really no reason for Lorelai to be nervous, it was just that talking to her Mom was still kind of an adventure, and not the kind any sane person would enjoy.

Taking a very deep breath, Lorelai picked up the phone and dialled. She waited three rings, and almost considered pretending she thought no-one was home and hanging up, when suddenly a maid answered. She stated her name and asked for her mother, waiting all of a second or two before Emily came on the line.

"Lorelai if you're calling to cancel Friday night dinner..."

"No, absolutely not. Why would I ever want to miss such a wonderful family event?"

The silence on the other end of the line was deafening and Lorelai was happy to just let her joke go and get on with the point of the call.

"Anyway, the fact is, Rory has been so busy with Chilton, she's hardly seen her friends," she began, thinking maybe it was a little rich sort of pinning this whole thing on her daughter, but Emily was just way more likely to be kind to Rory's plight than to Lorelai's own and they all knew it. "I know she's mentioned her friend Jess to you before. Well, there was supposed to be kind of a sleepover going on this weekend, plans have gone a little askew, so either I leave Jess alone in our house Friday night, or..."

She deliberately left her sentence hanging, in the vain hopes her Mom might catch on. She did.

"You want to bring Jess over for Friday night dinner," she guessed. "Well, that's absolutely fine, Lorelai."

A breath came flooding out of Lorelai that she hadn't even known she was holding in.

"Really?"

"Well, of course. Any friend of Rory's, especially a friend in need, is certainly welcome at my table," her mother told her definitely. "Of course a little more notice might've been nice, but I suppose you called as soon as you could."

There was a grin on Lorelai's face then. She was amazed, stunned, entirely floored by her mother's kindness to some teenager she didn't even know. Of course the fact said teen was Rory's BFF probably swung the balance. Had Lorelai wanted to bring a friend of her own to dinner, she knew the answer could be entirely different. For now, she was going to take the win that had got her out of a sticky situation with Luke, Jess, and Rory.

"Well, alrighty then," she smiled. "Thank you, Mom. Really, thank you."

"Don't go over the top, Lorelai," her mother snapped anyway. "It's not as if I'm some monster."

"No, of course you're not," he daughter replied quickly. "So, the three of us will see you tomorrow night."

Lorelai hung up quickly and spent a full minute staring at the phone in her hand, wondering at what just happened. It might've been longer if not for Michel's voice rising in volume as he got into a heated debate with an inn patron about flickering lights. Time to step in and do what she did best.

* * *

"Are you okay?" asked Rory, watching as Jess messed with his shirt some more.

She wasn't sure if he intended to have it tucked in or hanging out. Most often he didn't exactly look what a person might call smartly dressed. She guessed Luke suggested the effort. As much as she loved her BFF, Rory doubted Jess was thoughtful enough to dress up for her grandparents. Man, he looked uncomfortable, and Rory supposed she understood. Her Mom always looked freaked about coming here, but at least she had reasons.

"I'm fine," Jess snapped a little, though he hadn't meant to. "I just... I don't exactly know a lot of grandparents," he admitted, running a hand back over his overly-gelled hair and shifting awkwardly beside his friend.

It made Rory feel awkward too, remembering that Jess had no Grandma or Grandpa of his own. He didn't even have a Dad, or a Mom most of the time. Just his Uncle Luke really. She leaned into him a little, bumping his shoulder with her own.

"It'll be fine," she promised. "You can share my grandparents, I don't mind."

"Oh, honey, that's just mean!" Lorelai admonished her, not quite as sarcastic as Jess expected her to be. "Why? Why would you make your best friend share in that kind of pain and suffering?"

Jess smirked at the joke. Rory didn't.

"I love Grandma and Grandpa," she said grumpily.

"As do I," her mother assured her. "But that doesn't mean they're quite so warm and fuzzy to everybody as they are to you. Remember that!" she advised before turning her attention to Jess. "Stick close to me, kid. Any heat from Emily naturally gravitates towards me. I make a good deflector shield that way," she winked.

"Duly noted," Jess nodded once, and then took a deep breath as Rory finally rang the doorbell.

It didn't take long for a maid to come rushing, and then they were being ushered into the foyer of the over-sized house. The only buildings Jess had been in of this size were schools, hotels, and museums. They sure weren't houses. Actually, he considered, this place could be a museum, with all the vases and statuettes and such.

"Hello, Lorelai, Rory," Emily was suddenly greeting her daughter and granddaughter, and Jess turned quickly from his snooping when he heard his name come up.

"Grandma, I'd like you to meet Jess Mariano," Rory introduced all properly and politely. "Jess, my Grandma - Emily Gilmore."

"Good to meet you, ma'am," he said more politely than he had ever been heard to speak to anyone ever, at least Rory thought so.

He practically bowed when he said it too, and she was almost proud. At least she thought she had every right to be until she looked at her Grandma and saw her eyes get very wide. Maybe she had noticed that Jess' shirt wasn't tucked into his pants all the way around...

"Jess? This is Jess?" Emily asked, looking from the teen himself to Rory then Lorelai and back again. "It can't be."

"I was me last time I checked," he replied, with the slightest of sarcastic tones as he looked down at himself as if to check who he actually was.

"But Jess is your best friend," Emily stated pointlessly, at which Rory nodded.

"Since the sixth grade, yeah."

Lorelai wasn't entirely sure where this was going, but she started to get a clue just before her mother opened her mouth to speak again. If only she had been faster she might have avoided the outburst that reached wince-worthy levels of embarrassing inside only five syllables.

"But Jess is a girl!" said Emily too loudly.

"Huh," replied Jess himself, looking to Lorelai for help. "Now I'm just offended."

"Uh, Mom," she cut in fast, literally turning her mother towards her with hands at her shoulders. "Maybe I can explain. See, Rory's best friend Jess, he's a boy," she said slowly, as if explaining the alphabet to a small child. "Now, I understand that you probably assumed that Jess was short for Jessica or Jessamine or something else female, but it's not," she confirmed, then gesturing towards her daughter's friend. "He's just Jess, and we like him that way, okay?"

Jess tried for a winning smile, but it came out just about as awkward as he felt, all hands in his pockets and eyes everywhere but on Emily. Rory didn't know whether to laugh or cry. Her Grandma was always kind to her but she had the ability to be pretty scary sometimes, if riled. Now she had embarrassed Jess as well as herself in the space of barely five minutes, and that couldn't be good. Still, it was at least a little funny that she had assumed Jess was a girl. Of all the guys Rory had ever met, Jess was the least girl-like she could think of right in this moment. She bit her lip.

"Why don't you come through to the living room, Jess, and Richard will get you a soda," her Grandma said then, with a smile that might've been genuine, maybe.

Of course, Rory went with Jess, and failed to realise that Emily hung back on purpose, grabbing onto Lorelai's arm and leaning in to her ear.

"Lorelai, we will discuss this later," she said in severe tone her daughter was all too used to hearing.

"I'm sure we will, Mom," she sighed - it was going to be a long night!

* * *

Jess made a big deal of chewing on the food in his mouth for as long as possible before swallowing. Maybe fancy manners weren't his strong point but he did know he couldn't be expected to talk with food in his mouth. If he just kept chewing long enough he could get away with hardly saying a word as Richard and Emily tried to grill him on everything from his school work to future plans and dating too. Squirming was not a good look for him, Jess knew, and so often he looked across the table at Lorelai, hoping to be saved. She tried her best, she really did. Rory's Grandpa seemed okay with subject changes, but not the Grandmother, no way.

"Yes, Lorelai, it's wonderful that the inn is so busy," she said snippily, as the main course was exchanged for dessert. "But I don't think Jess was done explaining why exactly he finds school so easy to shrug off as if it were nothing."

"He didn't say that, Grandma," Rory quickly defended her friend, even as he opened his mouth to do it himself. "Jess is a good student, he is, it's just, well, sometimes he gets bored, because mostly, he's just too smart for the classes."

"Rory," he groaned at her explanation, one hand going to his forehead like he felt a headache coming on.

Honestly, that was half the problem. It was a compliment, and Jess did appreciate it, but at the same time he knew where it would lead. If he was too smart for Stars Hollow High, why wasn't he at Chilton with Rory? That would be the next line of questioning and he just couldn't take it. These people were not going to understand his life choices, and he couldn't care less about it, except the last thing he ever wanted to do was upset Rory or even Lorelai. That meant holding his tongue and staying put in his seat even as the grandparents drove him around the twist!

"Honestly? You should see the boy read," Lorelai jumped in fast before her parents could. "Hey, Dad, pick one of your classics that you love and make that the next topic of conversation. I'll bet Jess would be way more comfortable then," she said pointedly.

"Really?" asked Richard with interest then as the dessert of something looking distinctly like pudding was laid out in front of everybody, in crystal bowls no less. "Well then tell me young man, have you read the Russians at all? Tolstoy? Chekov?"

"I made it through War and Peace once, but I don't think I'd do it again," Jess said seriously, as he picked up his spoon and poked at his chocolate pudding with genuine confusion. "And who doesn't appreciate Chekov? Y'know the guy started the whole idea of the stream-of-consciousness technique. Without him James Joyce would've been lost in the woods," he frowned then, looking to Lorelai for help. "Just so I know I'm not going crazy, this is pudding, right?"

"It certainly looks like it. Mom? Are we crazy?" she asked Emily in earnest, as Rory bit her lip and tried not to laugh.

This evening was getting stranger by the second, that much was for sure. It was nice though, that Jess seemed to have impressed her Grandpa with his book smarts. Grandma seemed underwhelmed, but at least her attention was on Lorelai now. It wasn't as if it was news when Emily and Lorelai bickered anyway.

"You know, Jess, I think next time you come to dinner I should lend you a few volumes from my library," Richard considered when the pudding debate finally came to a close. "Are you free next week?"

"Er... I don't know... sir," he faltered, hating that he was making an idiot out of himself in front of these people and that he even cared in equal measure. "I mean, thanks, but next Friday is Rory's birthday so nobody is coming here, right?"

Lorelai visibly winced and Jess knew he just said completely the wrong thing. He dropped his spoon down into his dish and sat back in his seat. This could not get any worse from here. A hasty exit might yet be necessary and he wanted to be ready.

"Well, of course Rory and Lorelai will be coming here next Friday, that's the deal we made," said Emily haughtily, with just a hint of a smirk.

Jess wondered what that was for. Sure, she thought she was clever, he got that, but there was something going on here that he and Rory didn't know about. He was sure of that because she looked as confused as he felt, and Lorelai just looked awkward as all hell.

"Mom..." she began, visibly squirming.

"The deal?" Rory checked. "I don't understand."

"Oh, hon, I didn't... I was meaning to explain," she said with a winning smile that was as fake as... well, nothing in this rich house, Jess would guess. "Okay, excuse us," she said then, getting up and gesturing for Rory to follow her out of the dining room.

Jess moved to get up too, but then he wondered if he was welcome in the alternate conversation. He tried to catch Lorelai's eye but she was so fast in getting to Rory she didn't even look over. He watched the Gilmore girls disappear out into the foyer and squirmed in his seat. Neither of them noticed, they were dead set on having this conversation of theirs apparently. Jess tried to hear what was said but the door was swiftly closed. He looked first at Emily and then at Richard, finally back at his food. He so didn't want to be here right now.

Out in the hall, Rory took in her Mom's explanation and then half-exploded at the news.

"I can't believe you didn't tell me before!" she said, folding her arms over her chest and looking cross, or as cross as Rory ever managed.

"I'm so sorry, hon," Lorelai apologised profusely and genuinely. "I meant to tell you. I _wanted_ to tell you, there was just never a good time," she tried to explain, keeping her voice low just in case they could be heard. "The last thing I wanted was to make you feel guilty about these dinners and going to Chilton. Please, Rory, don't start feeling bad," she urged her when the negative emotions played across her daughter's face all too quickly. "I made this choice for you, because I thought it was the best for you, and maybe I should've consulted you first but it's done now. Are we okay?" she tried when she got no immediate answer, putting a hand to the teen's shoulder.

Rory shifted as if to shrug her off but didn't quite go through with it. She sighed, knowing there was no point staying mad about all this, especially not here at the grandparents house of all places. Her Mom had made a very big sacrifice for her, she knew that, and having to be here every Friday for goodness knows how long was probably punishment enough for Lorelai.

"Sure, yeah. We're okay," Rory acquiesced, her arms dropping to her sides at last. "I just wish you would've told me before."

"Me too," her mother agreed, looking shame-faced still.

"So, I'll be spending my sixteenth birthday here?" Rory was asking when Jess finally appeared.

"No way," he said definitely, closing the door to the dining room behind him - he just couldn't stay in there a moment longer with those people!

"Jess, apparently we don't have a choice," Rory shook her head sadly, but he was having none of her negativity.

"Sure we do," he realised, looking from her to Lorelai as he lowered his voice. "We've arranged a party already, the people are invited, we can't undo it. Isn't that, like, really bad social manners?" he guessed, sure that was the one thing that the elder Gilmores wouldn't want to screw with.

Lorelai smiled at his devious streak, but then frowned immediately after.

"Well, yeah, but the party isn't organised yet," she reminded him quietly. "That would mean lying to my Mom and whilst it wouldn't be the first time, I'm not..."

She hadn't finished but Jess didn't care. He was half way back to the dining room before any more could be said, even as Rory called after him to stop. The Gilmore girls shared a worried yet intrigued look and then hurried after him. Before they knew it, all three were stood in the dining room, looking down at a surprised Emily and Richard, still in their seats.

"I'm real sorry, Mrs Gilmore, Mr Gilmore, there's been a misunderstanding," said Jess, all in his best manners, hands braced on the back of his chair. "See, I didn't know you had a deal with Lorelai for her and Rory to come here every single Friday, and since next Friday is Rory's birthday, I organised a party. A big one," he emphasised deliberately. "I don't really think it would be right of me to let everybody down by cancelling or moving the date of something that big and complicated this close to the event."

Emily's eyes narrowed and Jess' knuckles went a little whiter, but he didn't flinch. Rory would've been impressed if she weren't panicking on the inside. Lorelai was similarly afflicted right now.

"_You_ organised the party?" asked Emily then, managing to look down on Jess even though she was seated and he was standing. "All by yourself?"

"Yes, ma'am," he nodded once, mindful of the fact that if she thought for a moment Lorelai was in on this there would be hell to pay. "I'm sorry, if I knew it was going to mess with your plans... Well, I didn't know. How could I?" he shrugged easily.

She didn't look convinced, and yet he was pretty sure Emily wasn't going to call him on it. She didn't know him well enough to tell he was lying. Most people that did know Jess couldn't do even that. Besides, all this impeccable manners crap that people like her stuck to, as well as the grandparents affection for Rory, ought to swing this thing.

"Well, we certainly don't want to ruin this party any more than we already have," said Richard at last, grabbing everyone's attention away from a stone-faced Emily. "As it is the surprise has gone out of it," he sighed, looking from Jess to Rory. "I'm sure you can come to dinner on Saturday instead," he smiled at his beloved granddaughter and daughter both.

"Sure thing, Dad. We can do that," Lorelai agreed with an unbridled grin that would not shift.

"Absolutely," Rory nodded her agreement, as everyone moved to retake their seats around the table.

"Excellent. Well, that's certainly fine with us, isn't it, Emily?" Richard said to his wife, even though it was clear to all that she would rather die than give in.

Unfortunately, her choices were limited in front of company and after Richard had already given his agreement.

"Yes, indeed," she forced out though teeth and lips that looked as if she just sucked on a particularly sour lemon.

Lorelai tried to temper her grin but failed miserably as she thanked her mother for being so gracious and reasonable.

"That's really great of you," she said, though her eyes had already shifted to Jess by then.

Oh, but the boy did look proud of himself, and honestly Lorelai couldn't deny he had every right to be. Not many people took on Emily Gilmore and won, and no doubt at a later date he would live to regret such a thing, as many had done before him. For now, they were all willing to take the win. Rory was going to get her Sweet Sixteenth party, on the right night, in Stars Hollow, where it belonged.

"Y'know, you should come," said the girl herself then - Lorelai dropped her spoon into her bowl in shock as she realised what Rory was doing - "To my party, I mean. If I'm having a party, I want you guys to be there," she said, looking from Emily to Richard and back again.

"We weren't invited," her grandmother said, with a glare towards Jess who paid no mind to the look.

"Well, I'm inviting you now," Rory insisted. "It is my party after all."

"That it is," Jess agreed, before shoving his spoon into his mouth, eyes never leaving the dish of pudding.

"Certainly we'll come, Rory," her grandfather agreed easily, almost completely unaware of the way his wife continued to squirm, or how much Jess was trying to hide his smirk in his dessert. "We'd be delighted."

"That's just great, Dad," Lorelai told him, still smiling, even as she shifted her feet under the table and lightly kicked the boy opposite her to stop his smug look. "Okay, back to... pudding," she ended with an odd look as she reassessed what had just happened here.

Between Jess getting Rory's party confirmed and the serving of the least classy dessert in the history of the world, it had to be the weirdest and yet best Friday night dinner so far!

_To Be Continued..._

**A/N2: Longest chapter so far, and my favourite too. What do ****you**** think? Please let me know, even if its a very short review. Thank you :)**


	9. Chapter 8 - 24 Hour Party People

**A/N: 6 reviews on my previous chapter? Count 'em - 6! Thank you all so much, it means a very lot to me, you lovely people :)**

_**(For disclaimer, etc. - see chapter 1)**_

Chapter 8 - 24 Hour Party People

"I have soooo many ideas for this cake!" Sookie declared, grabbing Rory's hand and dragging her toward the kitchen to taste samples and hear plans.

"But I was..." she protested weakly, looking back at her Mom and Jess where they were sat on the couch still.

"It's okay, hon, we got this covered," Lorelai smiled kindly, trying not to laugh as her baby girl was bodily removed to the kitchen.

Sookie meant well. She had been given the cake to take care of, and all the sweet treats for the buffet of wonder for Rory's sweet sixteen. Luke was going to provide the savoury side of things, and was making way less of a big deal out of it. That left Lorelai and Jess with decorations and invitations, a bigger task than it seemed actually. This party really had to be the biggest of big deals after the way it was pitched to Emily and Richard, for fear they might see through Jess' ruse if it wasn't an extravaganza of epic proportions. Of course, Rory deserved such a big bash for her special birthday anyway, so there was never any doubt this party was going to be a knock-out. Her nearest and dearest sure were going to make certain of that.

"So, I haven't really had a chance to say this without Rory here," said Lorelai, looking to Jess. "She likes to defend my parents as if they were saints, despite all her past experience... Jess, I am so sorry for the way they spoke to you. Mostly my Mom, actually, Dad really seems to have taken a shine," she grinned then as she watched the boy practically blush. "Who knew you gave good parent, huh? Or grandparent from your perspective, I guess... Whatever."

"Yeah, well," he shifted awkwardly at the other end of the couch, turning a cocktail umbrella around and around between his fingers. "I just didn't want Rory to have to spend her birthday with those people. I mean, I know they're your parents, but..."

"Oh, no buts necessary, my friend," said Lorelai definitely as she double-checked her guest list and scribbled on a couple more names. "Believe me, there's nothing you could say about dearest Emily and Richard that I haven't already said myself, especially my Mom. I think you handled yourself very well, Jess. Better than they deserved, that's for sure."

"You're not the only one who knows what it is to have parents that suck. Your Mom and my Mom should get together and go bowling," he smirked at his own joke a moment, watching Lorelai's lips curve too. "Besides, I wasn't gonna make Rory feel awkward or anything," he shrugged, throwing the umbrella aside and pulling his leg up under him as he turned sideways to face Lorelai more. "I want this party to be good for her, she deserves it."

"She does that," she agreed with a nod as she stared down at her legal pad still. "Hmm, I still can't decide if I wanna invite Chris to this shindig or not," she said in a low voice. "You got an opinion on that?" she asked Jess, but his eyes remained on a spot somewhere on the floor, completely unfocused. "Hey, Spicoli! Look alive!" she urged him, slapping him lightly on the arm. "Jess, seriously, what's up? You just turned all zombie on me. That's not like you."

She looked genuinely concerned and Jess couldn't help but smile. His own mother had been pretty much out of the picture since he moved to Stars Hollow aged eleven. He saw Liz maybe three or four times in the last five years, and he never even knew his father. Sometimes it hurt to think about all that he missed out on, and it was easy to be jealous of how lucky Rory got with her Mom. Other times he was just happy to have the weird quasi-family he had found here in this crazy town.

"You got Rory's gift yet?" he asked at last.

"Yes, but I am not going to tell you what it is," she said definitely, and with a grin she just couldn't help. "I know you two, closer than Benny to the Jets, and it would be soooo easy for you to let slip with my surprise, especially if Rory started probing for info," she said, tossing her list on the coffee table and declaring it done for now. "How about you?"

"I don't know," he shrugged as he made his admission. "I mean, usually it's easy. We buy each other books, CDs, nothing major, but this is her sixteenth birthday and... and I don't know," he muttered, making a big deal of looking anywhere but at Lorelai.

It was so cute when he got all shy and silly like that. She never told him so, because guys didn't like that, especially guys like Jess that thought they were tough. Lorelai fought to remember what Rory had bought him for his sixteenth a couple of months ago and was coming up blank at first, then she recalled it and frowned a little.

"Well, didn't she get you a book for your sixteenth?" she checked, already sure she was right.

"Yeah, but that was different," he told her definitely, but when Lorelai still look bemused he knew he had to explain. "That was a first edition Hemingway from the twenties. You know what that's worth? We're talking a thousand dollars minimum," he explained. "And yeah, I know, she got lucky in a weird rare book store out of town and she didn't pay that much for it, but that's still an amazing gift."

"Granted, it is pretty amazing if you're into Hemingway... and I know you are," she added with a look.

"Besides," Jess continued as if he hardly even realised she'd spoken. "Rory's a girl, and it's a bigger deal buying gifts for girls."

Lorelai opened her mouth to speak again and then closed it again quickly. Jess never really referred to the gender difference between himself and Rory. Actually, Rory didn't either. Of course they knew they were a boy and a girl, unlike most best friends that tended to be of the same sex, but it was never a topic for discussion. They had been friends since the age of eleven, when nobody cared about things like gender differences. Just lately, Lorelai had a feeling that Jess was starting to think more about this BFF relationship he and Rory had going. He sure was jealous of Dean, she knew that much, even though Rory wasn't even really dating the guy... yet.

"Jess, whatever you normally buy for Rory, she always loves it, so go with the same instinct that got those gifts and just buy something," Lorelai advised. "She's not going to care if it's expensive or flashy. That's not our Rory," she reminded him gently.

He nodded that he agreed with her, even as Lorelai walked away to answer the phone. Jess heard the name 'Max' spoken before she dodged upstairs to continue talking. His brain was too busy with other things to worry about Lorelai potentially dating a Chilton teacher.

Lorelai was certainly right about Rory, of course she was, but it didn't stop Jess worrying. He needed to get Rory something special. Sweet sixteen was a much bigger deal for chicks than it was for guys. There was no big party for his birthday, he had vetoed that the minute Luke suggested it, even when Lorelai and Rory tried to jump on the band wagon. For Rory herself, there had to be a fuss - a big cake, a party, and special gifts. If only he could think of something good enough for her.

* * *

Rory volunteered to go over to Sookie's house to fetch a few things she had forgotten just as soon as the suggestion was made that somebody needed to go. Honestly, she loved Sookie, and she loved her Mom too, but Rory needed to escape the crazy for a little while. Jess had left a while back, and all Lorelai would say was that he had to go shopping. Being like most guys, Rory knew Jess hated to shop, but the look on her Mom's face suggested maybe he wasn't buying for himself. That made her smile.

Rory was just checking the list of things Sookie needed from her place, or from the store if it turned out she didn't have them in her kitchen. She was so engrossed in her reading, she didn't realise someone was coming the other way until she had run headlong into his chest.

"I'm sorry!"

Both Rory and the stranger apologised in tandem, only to look at each other and realise they weren't strangers at all.

"Dean, hi," she blushed, just because she always seemed to whenever he was around.

Rory didn't know exactly what it was about this guy that made her so nervous. Sure, he was cute, friendly, and entirely sweet, but Rory wasn't usually the kind to go so girly over a boy. Dean was just special, she supposed, and though the two of them weren't exactly dating as such, they definitely got along well. Before long, Rory would like to be calling Dean her boyfriend. Of course, she wasn't about to tell him that, because that would be way too embarrassing.

"Oh," she said when she suddenly realised she had spaced out while he was talking, so taken was she by his beautiful eyes and dazzling smile - and apparently she was turning into a Disney princess all of a sudden! - Rory cleared her throat and spoke properly. "Um, I was just picking up some stuff for Sookie, my Mom's friend, she's working on my birthday cake..."

"It's your birthday?" asked Dean, since obviously this was news to him.

"Yes, well, no," said Rory awkwardly, pushing her hair behind her ear for the third time in some ridiculous nervous habit that she hated. "I mean, it is my birthday, but not today. On Friday, actually. We're having a party," she smiled. "You should come."

She blushed all the harder the moment the words were spoken and had the weirdest urge to run. At the same time, Dean's gaze stuck her to the spot and somehow seemed to prevent her from breathing until he suddenly spoke.

"Hey, I would love to come but I'm working Friday night," he sighed. "I'm sorry."

"No, it's fine," Rory shuffled her feet. "I mean, working is important... and good for you. I mean, not for your health exactly, although I'm sure it is, I meant... Well, money is good, and working earns money. Probably not much when you work for Taylor, but still, better than nothing, right?" she rambled the way only a Gilmore could.

Dean seemed to find it all very sweet and amusing as he was grinning again within a second.

"I'm not sorry to have the money," he agreed with a nod. "I mean, cash means I can buy gifts. Y'know, when people have birthdays?" he winked, and then suddenly he was walking away, with a cheery wave and a 'see you around, almost-birthday girl'.

"See you later!" Rory called back, before turning and fairly pelting to Sookie's house.

Falling in love was wonderful in its way, but if she blushed any harder, her face was going to explode, she was certain of it. That was the part Rory hated and loved all at once. She couldn't stop grinning as she continued to run a few more steps, then abruptly stopped. There was a reason girls like her were academic, not athletic. She slowed to a sensible walk and continued on, still smiling so widely her face ached. It was wonderful.

From behind the counter in the diner, Jess watched Rory speed by and wondered what was up. He very nearly ran after her, except he noticed even in her hurry that she was smiling. Nothing wrong there, she must just be excited about her birthday or something. That made Jess frown, not because he didn't want her to be happy about her party or anything, just because it brought his mind back to the whole gift buying thing. He had looked into the windows of every store in this back-water town on the way home, hoping for inspiration. He didn't find any.

Luke found Jess wiping the same spot on the counter that he had been on ten minutes ago and wondered what was wrong. Just when he opened his mouth to ask, his nephew looked over and caught him staring.

"What?" he snapped, not really meaning to but it still came out that way.

Luke had given up trying to reprimand him for little things like that. The way Jess was brought up, at least as far as age eleven, meant his manners weren't all they were cracked up to be. Mostly he was a good kid, no thanks to his parents, of course. Luke came down hard on the major issues, and let the small stuff slide for the most part. Honestly, he wasn't mad right now, he was just concerned. Jess was quiet and thoughtful on a regular basis, and Luke stopped worrying about that a long time ago. It was just the way Jess was. There seemed to be a certain mood he got in though, when Luke just knew something was wrong. Like Jess would like to talk about something but wasn't sure he could or should.

"I don't know," Luke shrugged. "You just, you seem like you have something on your mind. Were things okay at the Gilmore house?"

"Sure, yeah," his nephew nodded easily, tossing the cloth between his hands. "We got the guest list done, invitations, blah, blah, blah," he rolled his eyes as if the whole thing bored him.

Luke bit back a smile. He knew full well Jess didn't mind doing that kind of thing. Oh, he would if he were forced into it, or if it were for anybody else in town, but this was for Rory. Jess would go to the end of the world and back for that girl, and Luke didn't mind knowing it. She had been a hell of a good influence on the little hoodlum that had arrived in Stars Hollow five years ago and more. He couldn't be happier that the two were still best friends.

"Well, the food from this end is under control, and I can't imagine Sookie is having any trouble," he said easily. "Oh, I was going to ask you, I got this book for Rory..." he turned and reached under the counter, pulling a volume from a paper bag. "You think she'll like it? I mean, you two and all your reading, I figure you know what she has and what she'd like better than I would..."

"This is great," said Jess, almost sounding stunned as he turned the book over in his hands. "She loves Ayn Rand. I personally don't get it, but she does."

"I heard you guys talking about her once," Luke admitted. "But Rory doesn't have this book, right?"

"Nope. She only got into Rand's non-fiction recently. You're fine."

"Good," he smile, shoving the book back into the bag. "So, what did you get her?"

Luke knew that was a question better not asked when he saw a look of thunder pass over Jess' face. Maybe that was what had been bothering his nephew in the first place.

"None of your business," he muttered, pushing past his uncle.

Jess grabbed the coffee pot on the way and went to refresh the cups of various patrons within the diner. He was not at all happy to be reminded he had yet to even think of a decent gift for his best friend's sweet sixteenth, never mind actually go and buy it. Things never used to be so complicated where Rory was concerned. Jess never even saw it coming until the last few weeks, and he still wasn't willing to think about what had happened to them, for fear of what it would really mean going forward.

_To Be Continued..._


	10. Chapter 9 - Sweet Sixteen

**A/N: This chapter got looooong! I hope nobody minds that. Reviews are very much welcome, and I do thank those who take the time to leave the feedback - you're the best! :) FYI, I am purely a Literati shipper, so although there's going to be a little bit of Dean/Rory going on for a few chapters, I promise you it will not last, and the main focus will always be the Rory & Jess relationship, which will segue from friendship to romance in due course. Okay? Okay! ;)**

_**(For disclaimer, etc. - see prologue)**_

Chapter 9 - Sweet Sixteen...

"Welcome, my friends, to the show that never ends!" Lorelai ushered the next batch of party guests in through the front door. "Good to see you Patty, Babette, Maury. Rory will be thrilled you're all here."

"Well, we're thrilled to be here, sugar," her next door neighbour assured her. "Sixteen, Lorelai! Can you believe it? Sixteen!" she gasped.

"I know," Lorelai sighed. "Days like these, even I feel a little old."

"Oh, hush, sweetheart!" Miss Patty told her with a look. "If you're old, what hope is there for the rest of us?"

There was laughter aplenty as the new guests joined all the others. It really was a party, with people sat on every available chair and even some of the floor space. All the friends and neighbours had turned out for the occasion. Mrs Kim had even accompanied her daughter, much to Lane's chagrin, and Lorelai couldn't imagine anyone was missing from the fancy shindig with regards to good friends. The family side, well, on that they were running a little short, but Rory didn't seem at all concerned.

In the end, Lorelai had called Christopher to ask if he would be coming along. He made excuses, much like always, and said he would catch up with his best girls later. Lorelai couldn't help thinking that if they really were his best girls he would be there for them, not just on Rory's sixteenth birthday, but every day, always.

"Hey," said a voice behind her and Lorelai visibly jumped. "I'm sorry, I didn't mean to... I was just checking you were okay," Luke said quickly, feeling dumb.

Lorelai smiled.

"I'm fine," she assured him, turning and putting a hand to his arm. "You've been a huge help with all of this, y'know?"

"I didn't do much," he shook his head, shifting awkwardly. "It was just a little food."

"No, it was a _lot_ of food, and it eased a burden," Lorelai told him. "I mean, I love Sookie, I really do, but if she was in charge of _all_ the food, she would just get too many ideas and she'd go over-fancy. It was easier if you took point on the buffet and she mostly just had to handle the cake. Thank you," she smiled some more, leaning in to kiss his cheek.

Luke wasn't exactly the blushing kind but if anyone could reduce him to such idiocy, it was often Lorelai, or occasionally Rory. He was a bachelor, after all, who had learnt to be a father, in a way, but he couldn't ever quite handle the sentimentally of his two favourite girls.

"Like I said, it was no problem," he shrugged, reaching up to adjust his baseball cap in that nervous habit Lorelai found so adorable, even if she never did say so. "Looks like Rory's having a good time," he said then, glancing over into the living room and seeing her laugh and talk with her friends and neighbours.

"That she is," her mother agreed. "Seriously? She's being loved and spoiled with gifts galore. Sweet sixteen and not a worry in the world. What's not to be happy about?" she smiled, though there was a hint of sadness in her eyes, Luke thought.

He knew why, as everybody did. Though Lorelai never once regretted having Rory, the age of sixteen was not an easy ride when you were pregnant and essentially alone. This town had saved Lorelai and Rory, and then it had saved Jess in its way. For all that Luke complained about it, he had to love Stars Hollow for these things.

"Hey, mother of the party girl," he said, shocking them both by throwing an arm around her shoulders and giving her the briefest squeeze of a hug. "Stop looking so sad, you'll ruin the mood."

Lorelai laughed at that, sniffed back any tears that were coming, and stared up at the man who had so easily become her best friend these past few years. She never thought there would be a guy in her life like Luke, and she was grateful every day that she had met him.

"Don't ever make me find out how tough my life would be without you," she said, almost too seriously, and then she was walking away, leaving Luke literally opened mouthed and wide eyed.

Across the room, Rory greeted her Mom with open arms, and showed her some of the gifts she had been given in the past few minutes. Books aplenty, candy too, and some truly odd trinkets that only the people of Stars Hollow could ever come up with. With so many people sitting around in the living room, now seemed like a good time for cake, and yet Lorelai knew there was at least one person missing from the circle.

"Jess is still here, right?" Lorelai asked her daughter.

"He was," Rory frowned when she turned and realised he had disappeared. "Y'know, I think he's feeling a little claustrophobic," she whispered then. "You know he's not big on the mingling."

"I do know," Lorelai nodded once. "You want me to go look for him before we bring out the cake?"

"No, it's okay. I'll go," Rory smiled widely as she got up and picked her way through the gift wrap and ribbon all over the floor.

At the last minute, she came back and hugged her mother so tight, the two of them practically toppled over with the force.

"Did I tell you how awesome you are for buying me that computer?" she checked, even though they both knew she had already said it at least eight times.

"You did, but Mommy doesn't mind hearing it again," she assured her, hugging back for all she was worth.

"Where is she going?" Mrs Kim asked her daughter when Rory walked away then. "It is very rude to leave a gathering of people unattended."

"Oh, I agree, Mama," Lane nodded definitely. "But maybe she just went to the bathroom," she lied, knowing full well Rory was going after Jess.

Now Lane had the much bigger task of distracting her mother so she didn't come to realise that Luke's nephew Jess was the same person she and Rory hung out with all the time. She really hoped her own sixteenth birthday didn't turn out to be this stressful!

* * *

Rory walked though to the kitchen and found it empty, save for Sookie, who immediately stood in front of the cake and blocked it from view when she realised she was no longer alone. Apparently it was bad luck to see the cake before the candles were lit, which Rory was pretty sure was a superstition Sookie made-up herself, but she didn't argue. She held up a hand to keep her gaze away and slipped out the back door, wondering if she would find Jess outside. Turned out she really did know him as well as she thought, because there he was on the back porch steps, spinning a cigarette around and around between his fingers.

"Where'd you get that?" she asked with a serious expression, something that had long been known by the two of them as her 'withering stare'. "More to the point, _why_'d you get that?"

Jess opened his mouth to stay something but stopped short of actually doing so. He shoved the cigarette in the pocket of his jacket and waited until she sat down beside him.

"Jess..."

"Not enjoying the party?" he checked, deliberately making a subject change and they both knew it.

"You know I love my party," she grinned then. "You and Mom, and Sookie and Luke, you all did a great job of organising it, and I truly love it all," she assured him, leaning into his side. "Doesn't seem like you're having much fun though."

"I'm not a party person," he reminded her, as if she didn't already know. "I, er... I guess now's a good time for..."

Rory moved when she felt his body shift, wondering what it was he was trying to say. He left his sentence hanging and before she could ask him to pick it up and finish it already, she realised what he had meant when a pretty box appeared from inside his jacket.

"Happy birthday, Rory," he said with a smirk as he pushed it into her hands.

"Thank you," she smiled brightly, taking in the effort he had made with pretty paper and ribbon - it was so not like Jess. "You couldn't give me this inside?" she asked as she began to pull at the wrapping.

"Apparently not," he replied, but gave no real explanation for why they had to be alone.

The truth was, there was no reason, not really. Couples who were dating wanted to be alone because they just did. If you were giving important gifts like engagement rings and such then you wanted to be away from others. These were private important moments that your basic best friends didn't need to have. Jess closed his eyes a second and pushed all the dumb thoughts aside. Damn, he wished he had that cigarette lit before Rory appeared.

"Oh my God!" she gasped when she finally got her gift open. "Jess, this is... It's beautiful!"

He smiled at her enthusiasm and didn't doubt it was genuine. Rory had been known to get very excited over some truly weird stuff. As it was, this at least made some sense. It was only a pen, no fancy jewellery or anything that any 'normal' girl world think was awesome. Truth was, Rory wanted to be a writer, a journalist most likely. Writer's needed decent writing tools, Jess figured, and it suddenly hit him this was just the perfect gift, at least within his price range anyway.

"You're gonna be a writer, you gotta have the good stuff," he shrugged like it was nothing, but the way Rory was beaming from ear to ear did thrill him somehow.

"I never would've thought of that, I never expected, I... and it's so pretty!" she enthused all the more as she pulled the smart silver and gold coloured pen from its velvet lined box. "It's stylish but practical. It's perfect!" she continued on, and Jess rolled his eyes.

"Geez, anybody would think you liked it," he teased her, not quite ready for the way she threw herself into his arms a second later and held on tight.

"Thank you so much," she whispered near his ear as Jess hugged her back.

"You're welcome," he told her, wondering at the way his voice came out so soft and pathetic.

They hugged all the time. He'd bought her a hundred gifts over the years, birthdays, Christmas, and just because. It didn't mean that much and yet here in this moment, something inside of Jess flipped over in a disconcerting, kind of nice way that he didn't want to have to explain, not even inside his own head.

Things were changing, little by little he was noticing, and yet Rory didn't seem to realise it at all. It made Jess wonder if he was just being crazy, imaging things that weren't there. Anything else and he would come right out and ask, but this was maybe the one thing he could never talk to a female best friend about.

Rory pulled back some, still smiling, and met his eyes, but before Jess could even try to figure out what she was thinking the back door opened and Lorelai stepped out under the porch light.

"Hey, you two!" she called to them. "You're holding up the festivities in here. The natives are restless for cake, party girl!" she told her daughter, who scrambled up from the steps and rushed to show off her wonderful gift.

Jess got up to and dutifully followed the Gilmore girls back into the house. He nodded and smiled, taking Lorelai's praise over a perfect gift with as much grace as he could manage. He wondered what she would think if he told her he thought maybe his friendly feelings for Rory were changing in a more adult direction. Right now didn't seem like the time to ask anyhow.

As soon as they entered the living room, the lights went out and Sookie presented an over-sized cake, complete with Rory's picture painted onto the icing. It was a crazy idea, but it kind of worked, and his best friend looked so overwhelmed and happy as she blew out her candles after an overly loud rendition of Happy Birthday To You.

Jess stepped back as so many others piled in to hug the birthday girl and claim their piece of cake. He was somewhere by the door when Luke found him just staring, as if into space.

"Hey, you okay?" his uncle checked.

"Yeah, sure, why wouldn't I be?" he replied, though his eyes and stance never shifted at all.

Luke knew something was wrong, and not just tonight. It was hard to explain, but Jess had been quieter, more thoughtful than ever before these past few weeks. Luke started out thinking it was just Rory's absence from school and such, but they seemed to have patched things up on that score. The best friends were as close as ever, and they were at her party after all, it would make no sense for some rift between Jess and Rory to be the issue, but something was definitely wrong.

"I don't know, I just thought you'd be in the middle of things," he said carefully, watching Rory a moment and then bringing his eyes back to Jess' expressionless face. "You're the best friend after all, and you organised most of this, at least that's what you told the Gilmores, apparently," he added the last part in a low voice.

Finally he seemed to have Jess' attention, but Luke's victory was short lived. He realised his nephew was no longer looking at him, but past him, towards the front door.

"Speaking of," he said, pushing off the wall and heading over the Rory's grandparents. "Mr Gilmore, Mrs Gilmore. So nice to see you," he greeted Rory's grandparents with his best fake smile that Luke knew too well, still it was a pretty impressive show he was putting on, and Rory would certainly appreciate it.

"Well, thank you, Jess," Richard greeted him politely with a gentleman's hand-shake. "Is my grandaughter somewhere in this... crowd," he said as diplomatically as he could - Jess smiled at that.

"Right this way, sir, ma'am," he said, smirking more than he should when he caught Emily's eye.

She only glared, and that made him smile all the more.

* * *

Rory was having the best birthday. She had known her sweet sixteen was going to be pretty great given all the fuss that was made, especially with the party and everything. Her friends and family had sure done her proud, and spoilt her rotten. Her Mom got her a computer for school, Jess got her the most beautiful pen, her grandparents gave her money, and there was a pile of other gifts of all kinds that she loved - every single one!

Everyone was so kind and thoughtful, and they were all here to help her celebrate. Sure, grandpa looked awkward, and grandma looked mortified by some of the things Babette and Miss Patty said! Lane was constantly under supervision by Mrs Kim, and Jess just hadn't seemed to be quite the life and soul of the party, but it was okay, because he wasn't that guy, Rory knew. Jess would rather be alone, or at least alone with her, preferably watching a movie or reading a good book. Still, he was here, and he was the reason she was getting her party on the right day in the first place. For that, she loved him.

Of course, there was another guy in Rory's life who she liked in a whole different way. Love was too big a word right now, they weren't even officially dating, but she liked Dean a lot, a _very_ lot. He said he had to work and couldn't attend her party, but he had paged her five minutes ago and asked her to meet him outside. She made a fast excuse and slipped out the back door to see where he was hiding. There beneath the moonlight, she found him waiting, looking as nervous as Rory felt when she approached him.

"Hey, birthday girl," he smiled warmly.

"Hey, yourself," she replied. "I didn't think I'd see you."

"Me either," admitted Dean. "I hoped, but you know Taylor. He must have things just so before I can leave, and it was getting late, but... well, I'm glad I got a chance to see you on your birthday, to get the chance to give you this."

Rory smiled and blushed all the more as she took the haphazardly wrapped package from his hand. Carefully tearing into the brown paper, she felt giddy with the excitement of finding a bracelet inside. It was nothing fancy, and Dean immediately apologised for the fact. It was just a leather strap with a coin threaded on, but he had made it himself, and that meant so much to Rory.

Neither her nor Dean had any idea they were being watched. Jess stood at the kitchen window looking out and grimacing at the sight of his best friend being presented with the home-made trinket that made her smile and fawn like a Disney princess. Jess struggled to swallow the bile that rose in his throat, his fingers just itching to curl into fists. Man, he hated Dean Forester.

"Oh, that's where she went," said Lorelai as she appeared behind Jess and followed his eyeline. "Those two are getting pretty serious about each other, huh?" she asked him, and he fought to make any sound that wouldn't come out like an angry growl.

"I guess," he forced out eventually.

"Hm, I dunno how I feel about it," Lorelai considered. "I mean, he seems like a nice guy and all, but I don't know much about him. Hey, you guys go to school together, what can you tell me?" she asked the teen beside her, but he didn't answer, didn't even seem to hear the question. "Jess!" she prompted, smacking him lightly across the shoulder to get his attention. "This Dean guy, what do we know?"

Jess made a big deal of rubbing the spot she hit as if she just dislocated his shoulder. Like he hadn't had worse years ago, a _lot_ worse.

"He's an idiot," he grumbled, looking back outside at stupid Dean and giggling Rory.

Lorelai wasn't sure to make of that.

"Okay, so, the not good in English type idiot, or the gets into fights idiot, or the shoots up heroine down a back alley idiot?" she asked, all rapid-fire the way Gilmores often spoke. "Give me something here!" she urged Jess.

He sighed like talking to her was just hard work right now.

"Just the doofus kind of idiot," he muttered, before all but exploding into his next comment. "Why does he even need to be that tall? He's like the height of a building or something. It's ridiculous!"

Lorelai bit her lip and tried not to smile. She had suspected before that there was something brewing here. Jess did not like Dean, even before he knew anything at all about him. She didn't wonder at it. Rory and Jess had been the best of friends for more then five years now. He didn't want anyone else muscling in on that. The degree of jealousy Jess was feeling, that was yet to be defined, as were any possible changing feelings he was having in Rory's direction. It made Lorelai wonder...

"Jess, are we a little jealous of Dean and Rory's blossoming relationship?" she asked plainly with just a little sarcasm in play.

"Oh, geez!" Jess reacted with some apparent horror at what she was suggesting, but that was likely all bravado, Lorelai thought.

"What? You're showing me a lot of green-eyed signs here, grasshopper," she said definitely, the both of them now facing each other rather than the window, each holding their ground most definitely.

"He's not good enough for her, okay? That's all it is," he said, waving one arm a little too emphatically. "She doesn't even act like herself around him, she goes all girly and weird!"

"Jess, honey, she _is_ a girl," said Lorelai with a smile she hoped came out as kind as she meant it and not at all as if she were going to laugh at him - she really wasn't.

"You know what I mean," Jess muttered some more, but Lorelai wouldn't stop staring and grinning. "I gotta get out of here," he declared, storming off.

He blew straight by Miss Patty and Babette who were on their way to the kitchen with a pile of empty dishes and glasses for washing.

"Oooh, somebody's on the warpath!" said Miss Patty, watching Jess' butt as it disappeared into the living room.

"Everything okay, sugar?" Babette checked with Lorelai.

The smile was sure gone from Ms Gilmore's face now as she considered the real mess they could all be in for yet. If Jess wasn't just worried about losing his BFF to a boyfriend, if he liked Rory more than they ever realised before... Oh boy, things were going to get bad. Lorelai wasn't sure how she was going to deal, or how Rory would deal, since she was pretty sure her daughter had no clue Jess' feelings for her were changing so dramatically.

Before she had a chance to think any more about it, or even begin to try to find something to say to get the two nicest but biggest gossips in town off her case, Luke saved the day, just like always. He appeared in the kitchen doorway with his hand over the mouthpiece of her phone. Lorelai hadn't even heard it ring in amongst all the Dean/Rory/Jess drama!

"Lorelai, there's some guy named Max on the phone for you?" said Luke, waving the cordless in her general direction.

"Oh, thanks," she smiled genuinely at the sound of that name, grabbing the hand-set from Luke and wandering away. "Hey, Max," she greeted him, almost immediately giggling and fawning like a much younger girl.

Luke seemed to squirm at the sound of her laughter and the way she seemed so happy to hear from this Max guy. He told himself he just didn't like Lorelai dating Rory's teacher because it would be awkward and weird for the girl he loved like family. Of course, that wasn't really true. There was so much more to it than that and even though Luke would never admit it, not even to himself, Patty and Babette sure knew. The look they shared spoke volumes on what they thought about Luke and Lorelai's close friendship, but Luke never noticed for a second, since he was way to busy seething.

_To Be Continued..._


End file.
